


Just In Time

by Empty_Scribbles



Category: Gossip Girl
Genre: F/M
Language: English
Status: Completed
Published: 2015-01-29
Updated: 2015-05-20
Packaged: 2018-03-09 13:22:55
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 22,307
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3251267
Author URL: https://archiveofourown.org/users/Empty_Scribbles/pseuds/Empty_Scribbles
Summary: <blockquote class="userstuff">
              <p>Summary: Post Season 6x10 AU, past the flash forward where Dan travels back in time.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I believe this may have been done before, but this AU has always been in my head for a perfect post season 6 fic. Dan travels back in time, but the best part is that he's not the same person. He's post season 6 Dan, which makes things more interesting.

His marriage of 15 years with Serena ends shortly after dinner, on a late summer afternoon. The kids are outside, playing badminton with Aunt Blair. He hears them gasping for air and shrieking in excitement out on the backyard, driving all the crickets away. All the while their mother is standing beneath the dim ceiling light of the dining room, behind the shadows, trembling underneath.  
  
“What will happen to the kids?” She whispers, through her shaky congested voice. They’ve been at it for some time now and the only thing he can conclude is that the two are better off without each other.  
  
Dan presses his lips together and folds his arms across his chest. “We’ll have to wait and see on what the judge decides”  
  
“I won’t let you take them away from me!” Serena growls and pounds hand onto the dark mahogany table, leaving the leftover plates to jump up and rattle.  
  
“You don’t want them anyway!” Dan shouts back. He places his hand on the table and curls his fingers around the tablecloth, feeling his neck pulse.  
  
“What is going on here?” Blair asks, jumping into the deep and thick tension as she approaches through the doorway connected to the foyer. “The kids can hear you”  
  
“I’m staying at a hotel tonight” Serena answers and storms past them, up the staircase.  
  
“Take all the time you need!” Dan yells out, watching her ascend up the staircase.  
  
His eyes then fall to Blair Waldorf, his wife’s so called best friend. They were friends once, but that is nothing but a fable now. A story his children’s mother likes to share when one of them comes across his first novel.  
  
The brunette stares at him, dark curls draped over her bare creamy skinned shoulders, with the sound of Serena rummaging through things upstairs. Blair is not one to intervene anymore. Dan has given her everything that is his; his wife, his children, his home.  
  
Serena was deeply saddened to hear of Blair’s divorce. He spent nights listening to Serena whisper the nasty details of Blair’s failed marriage, as they lay on their bed, waiting for the sun to rise. Serena decided to take action and care for childhood friend shortly after. They knew Blair didn’t have much family and welcomed her in as the new member of their household.  
  
Her thin bony ring-less fingers wrap around the thick wood railing, but her attention remains on him. “Money has really changed you”  
  
His eyes drop to the shiny russet floorboards of the foyer. She doesn’t give him time to respond, as he hears her climb up the staircase to comfort Serena. But he’s used to it by now. They share very few words nowadays.  
  
  
  
  
  
 _I used you as leverage with Chuck. I was waiting for him to be ready for me._  
  
  
It recites in his head, over and over. The thought that he never stood a chance hurts more than just a simple preference. How bleak has his life become that he runs old conversations over and over in his head. He sighs and takes a sip from the mug of steaming coffee.  
  
“Hello Dan”  
  
He stares up and sees a petite teenage brunette behind the shadows of the entrance. She has the same creamy complexion of her mother and a small well aligned nose gifted by the gods. Her carmine red ravenous lips slowly curl into a smirk as she takes a step from the darkness and into the light.  
  
“It’s Mr. Humphrey to you doll” Dan says.  
  
She grabs a stool to join him by the counter, in the kitchen. His eyes try to refrain from dipping down to her thin spaghetti scrap dress as traces of peach catch his nose.  
  
She leers with her doe eyes. “Do you mind if I join you Dan?”  
  
“Chloe” Dan warns, jaw clenching tightly  
  
“What?” She reels back, feigning pure innocence.  
  
“You should be with your mother” Dan murmurs and stares at the small Degas painting of ballerinas. He hates that fucking painting. It’s going to be the first thing to go after he kicks Serena out.  
  
“The funny thing is that she’s here” Chloe tells him and he suddenly looks over. She arches a brow, small thin lips fighting not to curl.  
  
“You don’t realize what you’ve done” Dan says and shakes his head.  
  
“Don’t you understand?” A crease forms in-between her brows, face scrunched in disbelief. “She deserves this and I can’t believe you were going to let her get away with it”  
  
Dan turns his head away from her. “You’re just like your mother. You don’t think when you’re angry. You just want to inflict pain”  
  
“I’ll take that as a compliment” Chloe replies smugly and swiftly grabs the coffee mug to take a sip.  
  
“Don’t-“ He attempts to pry it away from her hands.  
  
“Mmmmm….Vodka!” She wiggles her brows and slides the mug back to Dan. “This is a cause for celebration, no need to hide the alcohol”  
  
He stares at her, feeling slight warmth growing in his eyes. “You’re too young to understand”  
  
“All my life I have asked you what the deal with Inside was, but you always waved it off, telling me to stop being such a persistent nag” She leans in, and her features harden as the smirk disappears. “So I did what you asked and ignored the drinking and long stares. But you cannot lie to me anymore and pretend this shamble of a marriage is worth saving”  
  
“So what? I should dump Serena with the kids and marry your mother so you can live out your stupid fantasy” Dan questions, staring at her incredulously. “You may prove to be smarter than all of us with your antics and schemes, but you still dream like a spoiled little brat”  
  
Her fingers curl into a fist. “I don’t dream, I make things happen”  
  
“Chloe” Blair calls, leaving Chloe’s doe eyes to bulge out “What are you doing up so late?”  
  
Her voice still sends a tingling sensation up his spine. He wishes he could erase her from his brain. Maybe he wouldn’t need the saving Chloe claims he desperately seeks.  
“Nothing” Chloe turns around the stool, smile ear to ear, like a little angel. “Just comforting Uncle Dan here”  
  
Blair folds her arms across her chest. “Upstairs” She then glares. “Now!”  
  
“But mooooooooom” Chloe whines and slumps her shoulders.  
  
“Chloe, I don’t want to hear it” Blair replies and places her hand on her hip. “After what you pulled today, you should be thanking the stars Dan is still speaking to you”  
  
“Fine” She huffs and hops off the stool, pouting her lips as she drags herself out of the kitchen.  
  
“I’m so sorry Dan” Blair apologizes and takes Chloe’s stool to sit by him. “Obviously my daughter doesn’t understand boundaries”  
  
He wants to laugh, so badly. How can Blair expect her daughter to be any different? But that’s what makes her so endearing and alluring to him. She has the power to rid the pain and sorrow of his marriage.  
  
She places her hand on his thigh, leaving his brows to furrow in deep confusion, as his eyes skim over her face.  
  
“I didn’t know Dan, I swear”  
  
He feels a lump form in his throat. “Would it matter if you did?”  
  
“I would’ve told you” Blair answers softly.  
  
He doesn’t want to believe her. It can’t be true. They rarely exchange words and are merely forced upon acquaintances. Serena has become the vine that binds them.  
  
“You shouldn’t be here” Dan whispers, feeling the heat of her warm skin. “Serena’s alone…And you’re not supposed to be nice to me”  
  
“I don’t want to go” She confesses.  
  
He lifts his eyes up to see her staring, and smiling nervously, her silver heart shaped necklace teasing along the neckline of her dark green half sleeve blouse. She places her hand on top of his, and he thinks he must be dreaming.  
  
“You don’t want to go?” He repeats slowly, thinking saying it twice may make it more real.  
  
She nods and stares into his eyes. “I want to stay here with you”  
  
His fingers curl tighter around hers, feeling the desperation of not losing her once again. He’s spent the past twenty years longing for her, watching his Blair change and transform into someone the Upper East Side didn’t recognize anymore. None of it mattered to him, because she was always there, under his skin, beating along his heart.  
  
Blair chews on her bottom lip, as her eyes fall down, hair falling over her face. “Do you ever wonder what it would be like if I fell in love with you first…Before Chuck”  
  
Dan blinks and huffs out a breath of disbelief. “Wouldn’t that be something?”  
  
  
  
  
  
He figures he isn’t in Connecticut anymore when he wakes up to the sound of construction and traffic. When he sits up on the bed, and looks around, he quickly realizes he’s in his father’s Brooklyn loft. The strangest thing about it is how old the model of the laptop on the desk is.  
  
His phone vibrates and he picks it up off the dresser to see a Gossip Girl blast.  
  
“What the hell?” Dan murmurs as he rubs his eye.  
  
No, he is definitely not in Connecticut anymore. The last thing he remembers is drinking with Blair in their kitchen, and teasing each other about high school.  
  
He grabs his old cellphone once again and checks the date.  
  
November 2, 2007  
  
Looks like he needs to prepare for his first date with Serena.


	2. Chapter 2

**Summary for the Chapter:**

> Summary: Post Season 6x10 AU, past the flash forward where Dan travels back in time.

**December 10, 2015**

He hates how his skin feels like it's shattering when he sets foot outside the airport and into the freezing wind chill. Not too long after Blair's wedding, he moved into Serena's Upper Eastside home. His agent proposed a move to the sunny west coast, and he's been sitting on it ever since.

When the elevator to their penthouse opens, he hears Serena's mother through the men hanging up the snowflake chandelier up on the ceiling and muffles an annoyed groan from escaping his lips.

He finds them sitting hip to hip on the white sofa bed, looking through the pictures of their trip to Dubai on Serena's tablet. They agreed on having a party as a couple for friends. His sister Jenny should be around as well, helping with the finishing touches for their party.

Serena has the most well thought of, exclusive parties, and he's glad to be a part of them. An invitation to meet her circle is one of the perks of being her boyfriend he's found. His new connections have led to experiences he's been able to transfer into writing and thankfully he isn't only writing about Blair anymore.

"Dan, I must say this looks like it was an amazing trip" Lily admires. "You two make such a gorgeous couple" She then scrunches her nose cutely, and smiles at Serena.

He meets Serena's eyes, and sees the desire she has for him in that moment. Something about Lily complimenting him always turns her on. It's one of Serena's many secret fetishes; having something her mother can't.

"Oh my god"

Serena clasps her hands excitedly, eyes wide in excitement with a grin that many envy.

"What?" Dan chuckles lightly.

She stands up and curls her arm around Dan's, barley able to contain her excitement. "You're here and we're going to be throwing party as a couple"

Dan lips curl in amusement as he turns his head to meet her blue eyes. The winter has ruined her beautiful tan shade, although she still remains something close to perfection. Her blue eyes seem to grow the longer they stare and he feels out of breath suddenly.

"S! A little help here!" Jenny shouts from the kitchen.

The fire alarm rings and the smell of something burning consume his nostrils.

She grabs the yellow striped apron off the coffee table and scurries over to the kitchen while tying the apron around her yellow strapless dress.

It leaves him with Lily and an unsettling feeling washes over him. There is always an issue they were never aware of floating over their heads and Serena's mother had a knack for being behind it. His jaw clenches tightly and a lump forms in his throat. He stands there idly, waiting on the cold hearted witch.

"I finished your book last night" She finally says, breaking the silence between them.

Her eyes narrow, giving him a death stare. Being around the Rhode's women web of lies is poisoning, but he's learned the grass isn't much greener anywhere else.

He puts his hands up in defense. "It's important to remember that it's a work of fiction"

"I consider myself to be a woman of very high intellect, so please do not talk down to me"

His eyes widen and a sinking feeling begins to form in his chest. "Lily, please consider it as a work of art and nothing else"

"Art?" She mocks and presses a hand on her chest. "No Daniel, we call this trash"

He swallows hard, trying to hide his slight dejection. He tries to remind himself that it is her way of gaining leverage. The last thing he considers it is trash. Maybe he did indeed write a character inspired by Serena as someone artificially beautiful. There was also a part in the book where the protagonist admits he thinks she dresses slutty to his friends. However, when he wrote it, he understood it wouldn't be taken well by the Rhode's women. He never ever meant to write about Serena, but it just naturally happened that way.

"Just tell me one thing" She requests and he lifts his eyes to meet hers. "Are you having an affair?"

He does his best to appear flabbergasted with her accusation. Acting is something he has picked up on residing in the circles of Manhattan's elite. He's become the biggest phony he knows, but the change has left him with more desolation.

"With who?" He asks as a crease forms in-between his brows.

"I can't tell" Lily answers bitterly, staring at him straight in the eyes, fearless as ever. "You left out details and the lack of description leaves the mistress's identity a mystery"

"I'm not having an affair" He tells her, meeting her eyes. "And I hope that you will bring some positive energy to the party tonight. I can speak for Serena when I say your behavior right now is unacceptable"

His threat finally shuts her up, as her lips press tightly and she lies back on the sofa. He gives her dirty look before straightening out the jacket of his two piece suit, and heading for the kitchen, with his polished dress shoes clicking against the marble.

When his phone vibrates, he reaches for his pocket and sees a text.

_When can I see you?_

He deletes the text before poking his head through to the large open-concept kitchen. The girls are plating the food on the island, underneath the three mini pendants and it appears the smoke from earlier has cleared. One of the things he loves most about Serena is that she prefers home cooked meals to catering. However, with the expected guests only growing, they decided to add some catering in as well just so Serena wouldn't be overwhelmed.

A smile becomes of his lips when he sees that his girlfriend and sister are wearing matching aprons. They both seem rather happy. Jenny has already given him her blessing to propose. She keeps on insisting Serena is the so called one.

He almost loses balance when someone brushes past his shoulder roughly, ruining his long gaze.

Blair looks over her shoulder and glares as she walks past him. "Get out of the way, Humphrey"

"Who invited you?"

He can't help it. She drives him mad.

Like always, she's dressed to precision. Her whole ensemble goes together. The chest of her thin strap dress is glittery gold, but the rest is black, with the remaining dress hovering just above her knees. She can thank god for the heated floor he supposes.

She places her white pearl necklace in-between her fingers as her doe eyes shoot daggers.

"Dan, be nice" Serena reprimands and warns him with her eyes.

It's not fair Serena always manages to jump in. His lips purse as he watches the brunette glare defiantly in his direction.

"I should go" He says and flickers his eyes over to Serena.

"Where?" She stares at him surprised and slightly concerned.

"The team wants to go over the numbers since the release" He tells her and then coyly rubs the back of his neck with his hand. "And I wanted to write…I feel inspired"

She places a curled fist onto her slim waist, and taps her heel impatiently, as she stares and thinks. Finally, she sighs and her shoulders slump.

"Just please be here before it starts" She pleads.

He nods, enthused he won't be doing any manual labor for the party. He then cups her face with both hands before kissing her on the lips and leaving their place.

 

 

 

So he lied about meeting with his publishing team. Instead, he tightens the scarf around his neck and hails a cab to the Waldorf penthouse, where Eleanor Waldorf still resides. Before leaving for Paris, mother Waldorf thought it would best to schedule him for a visit.

A nostalgic feeling runs through him when the elevator stops and the foyer to the Waldorf penthouse lies before him. It's hard to remember the last time he'd been there, mostly because he's been trying to forget. He doesn't stand around to take it in, rather, he heads straight for the office, thinking how lonely it must be for Eleanor with Cyrus waiting for her in Paris.

When he swings by the office, he peers through to see Eleanor focused on the task at hand. Her brows are furrowed in deep concentration as she flips through the pink sketchbook. When he clears his throat, she lifts her eyes and a welcoming smile appears before him. He can't help but meet her smile as well. Things have changed over the years and new allies have been made.

She greets him with a kiss and hug, and he can feel his heart grow warm.

"How was your trip?" Eleanor asks and gestures him over to the black leather chair in front of her desk.

"It was good. We finished on the renovations" He answers and takes a seat.

The first thing he did with his money was buy a house in Lake Como. It's always been a dream of his, living a life of romance outside America. As a child, he had a poster of an elegant faceless couple in his room, looking out of the terrace and into a lake that always reminded him of Lake Como. Of course it is very difficult to own property there, as most have to rent, but Serena was able to sway a homeowner to sell.

She leans back and stares, the corner of her lips curling. She's shared with him on multiple occasion of how amusing she finds him.

He tells her about his trip, and she listens, chimes in when she feels necessary, and even laughs at his unfamiliarity with the Italian culture. Serena has been teaching along the way, now that he has enough money to travel freely, but he still feels he has much to learn.

However, the mood shifts sooner rather than later when the laughing dies down and he's left with the look of deep sorrow. He's reminded he isn't there to tell her about his trip. She reaches for her drawer and places his new novel on the desk, fingers running through the letters of the crisp golden title.

"This one was very different"

"I wasn't very happy with Serena" He says lamely.

"I figured" She replies dryly.

"Um…" He shifts in his chair uncomfortably and readjusts himself. "As you know, I wasn't emotionally ready to be in relationship when I started dating Serena. But things have changed for the better and I think our relationship has never been stronger"

"I understand and that's why I brought you here" She sighs sadly and folds her fingers together, over his book. "Are you able to keep a secret?"

He nods in response and watches her stare down, avoiding his eyes. He figures it's big when the words aren't leaving her mouth. She has never been afraid to speak her mind, and the thought that she's having trouble is quite a frightening sight.

"Lily has shared with me that Serena was recently pregnant… but um…now she is no longer" Eleanor manages to say before closing her eyes in disappointment.

"I don't understand?" He leans in, feeling his voice break for the first time in a long time.

"I'm very sorry for revealing something so terrible, but you've been sharing a bed with this person and I thought you deserved to know" Eleanor explains and places her hand on top of his.

It's hard to say he knows who to believe because he's learned everyone in the Upper East Side has an ulterior motive. And yet he wouldn't put it past Lily convincing Serena.

 

 

 

Eleanor leaves, with the hired help rolling her luggage along into the elevator, leaving him alone in the abandoned Waldorf residence. With his hands in his pockets, he thinks and thinks, searching for the right answer.

He hears the elevator ding and looks over to see Blair Waldorf entering the foyer, holding an up to no good smile.

"Hello Humphrey"

He checks his watch and frowns. "I should head back to help Serena"

"Nonsense" She waves him off and walks past him up the staircase. "I have to show you something"

"What is it?" He asks his eyes trail up from her legs to her hips swaying as she continues to climb up the staircase.

"It's a surprise" She sings and he thinks he even hears her hum.

His curiosity wins over and he follows her up all the way to her bedroom.

"Blair, I don't think this is a good idea. Your mom jus-"

It turns out she's looking for trouble. She pushes him on the bed, and he falls back, a little surprised by her force. She shushes before he can finish, one finger on his lips and he suddenly gets lost as the scent of her hair shampoo trails up his nose. Dam her and her perfectly shiny dark chocolate curls.

He always dreamed of her crawling back to him, laying out the perfect opportunity for him to tell her to shove it. However, she did indeed come crawling back to him one night, long before Henry's birth. She cried and even begged when he turned her advances down. It was more difficult than he had ever imagined. Seeing her plead made his heart feel weak and it was then he realized how much he still loved her.

"Serena thinks I'm happy with Chuck" She tells him and pouts her lips.

"Your friendship is pathetic" He replies, lifting himself up to watch her.

"Tell me about it" She sighs and begins slipping the thin strap off her shoulder, leaving her creamy skin bare.

"I shouldn't be doing this" Dan says, sounding awfully distracted. Her dress drops to the floor, pooling around her feet, leaving him breathless at the sight of her tight thin black corset.

He falls back on the bed, and shuts his eyes. She makes his heart race. He has been trying to escape her, but she always manages to pull him back. He hasn't felt anything like being with her. He wishes he could get over her, but the only resolution would be moving away, and he doesn't think leaving the city to move on is worth not feeling love for her.

Her lips are on his, eyes shut, and before he knows it, he hears a click. It gets him hard, real hard.

She pulls her lips away when both of his wrists are handcuffed to her headboard, out of breath. "Did you follow my instructions?"

He shuts his eyes, trying to breathe steadily as he feels her fingers underneath his jacket. Abstinence was her order. When he left the city, he promised Blair he wouldn't even masturbate. The hardest part had been not having sex with Serena the week he was leaving. It caused quite a rift between them and now he's wondering if he fucked everything up.

What he likes most about Blair is that she's always coming up with something new to spice things up, even though sometimes he thinks she's crazy and unreasonable with her requests. The handcuffs leave him vulnerable, and with very little dignity, but he understands it's something Blair gets off on.

He loves it when she's demanding and likes to take control. Dan has always been more of an appeaser.

 

 

 

**November 7 2007**

Sure, he should be thinking about getting back, but he doesn't really know what he's going back to. He can't remember feeling this alive being married to Serena for all those years. It's a reset button, and for someone gifted by a greater power, he must take advantage of finally having the part of him that was missing. Serena is the key to being on the inside, and using her is just his way of making things right. If he's learned anything from living through his life, it's that Blair belongs with him.

He looks through his closet, seeking something nice to wear. He may need a new wardrobe because there is no way a teenage Blair would approve. He picks out a white slim fit dress shirt and does best with what he has to work with. Dan remembers picking out clothes blindly at this age. Looking good was something he found more appealing during later years.

After showering and getting changed, he joins the rest of his family out in the kitchen counter for breakfast. He finds Jenny absorbed on her phone while his father gestures him over to the empty stool.

"Morning" Dan greets and grabs an apple from the basket in the middle of the island countertop.

"Are you sure you're prepared to show your face in school?" Jenny questions, lips quirked in amusement as she remains entrenched in her phone.

A crease forms in-between his brows. "Why wouldn't I be?"

Jenny glances over and arches a brow. "Uh, did you forget what happened last night?"

Yes, he remembers it quite vividly actually. His lack of experience with the female gender caused him to make a fool of himself. He should've grown a pair and kissed Serena, but instead they were left with more of an awkward goodbye.

None of this matters because he knows the outcome. Serena is and will always be in love with him.

"Don't worry, I have a plan" Dan smirks.

There is only one way to make the most of his second chance at happiness. He has a plan and that plan entails of making a visit to the MET steps before class in the morning. He proceeds up the steps, all the way up until he's hovering over the girls, minions, a gorgeous blonde, and a queen. He's kind of losing his vision when he lays eyes on a beautiful teenage Blair, headband and all. It has been too long and part of him wants to cry.

She stares at him unimpressed, like who the hell is he to be on her steps. A smirk then forms on his lips and the two best friends stare back at each other for a minute before coming back to him. God does he ever love being back in school.


	3. Chapter 3

**Summary for the Chapter:**

> Summary: Post Season 6x10 AU, past the flash forward where Dan travels back in time.

**August 16th, 2013**

He spends the entire party sipping from his champagne flute, staring at Blair, in her beaded and sequined cocktail dress. She's smiling wide, putting on her typical endearing hostess act, but he's spent enough time with her to know better than that. His fingers would once yearn to write something derisive, to tell the world Mrs. Bass is not what she seems and there are many hidden secrets locked in a drawer. That article he posted through Vanity Fair was just supposed to be the beginning; yet, it became the last cutting expose. He never ended up writing a scathing story after all.

It starts with his sister Jenny. She opened a small local clothing store in Soho and it's been quite the little success. However Blair Waldorf gets off on squashing any threats. Like she's said on numerous occasions, fear is more important than love. And so his sister's shop is no more because she was buying high quality fabric for cheaper than the competition through the black market illegally. The worst part is that Jenny has no idea Blair had been the one to sell her out.

He waits for the party to end, until the hostess is all alone, shutting the last of the lights of her new townhouse. Her face quickly turns to stone when she sees him waiting in her living room, hands in the pockets of his pants.

She folds her arms across her chest and rolls her eyes. "Ugh, as if this day couldn't get any worse"

It's like she tries hard not to think about him.

"Why don't you tell me about it?" Dan proposes.

He can't imagine anyone with more pristine skin. Sadly, she is perfect and he knows it. Nothing can change that, which leaves his life in sort of dismay. There is nothing wrong with Blair, except her decisions with love. It took him forever to realize Blair is exactly who he thought she was, and loving her is not something he regrets any longer. He just wishes the outcome was different.

She huffs, but sits on the chaise anyway. "Fine, the sooner you tell me what you're doing here, the sooner you leave" She presses her lips tightly, scrunching her face at the sight of his shoes before staring up expectantly. "So, what can I do for you?"

"I want you to hire Jenny" Dan says.

She laughs and he sighs, waiting for her to end the mocking. Finally, when calms down, wiping off the slight tear of joy from the corner of her eyes, she meets his eyes.

"And why would I ever do that?"

"Because she's my sister" He answers self-assuredly, like that's supposed to mean something.

Her face becomes solemn unexpectedly, humor wiped away. Unlike her, he isn't scared of rejection, or putting himself out there. The best way to get Blair Waldorf to open up is being the first to admit something close to his chest. It isn't like she can break him any further.

"I uh-" He swallows hard and hides from her gaze. "I really care about you" He feels her eyes burning through him now. They're probably wide, and she's breathing deeply through her nose, taking his words in.

When she doesn't say anything, he lifts his eyes to see her staring at him with two big brown orbs that soften him instantly. Her smile appears more painful than pleased, and her breathing clearly slows down as her chest moves up and down more noticeably. Oh god, she's getting that cross-eyed look, making his heart flutter. He didn't think his heart would ever be capable of such a feeling. He's been desperately seeking the fluttering feeling again. It's like a drug and Serena is the substitute that doesn't quite make up for it.

He kneels down before her and slides his hand underneath her the soft skin of her calf, earning him a surprised gasp. He lifts it up ever so slightly, and slips her heel off to find her feet swollen. She always overworks herself, much to his displeasure because her husband is a bastard and doesn't know how to take care of her properly.

He begins massaging her foot and her glossy pink lips part open. It's quite the sight. Her wave of pleasure is clear, as he can see it on her face. It still amazes him how well he knows what his Blair needs.

"You're exhausted" He says quietly, working her lovely foot as her stubby little painted toes curl back and forth, seeking attention.

"Admitting such a thing would be a sign of weakness" She tells him before pursing her lips, and watching him carefully.

He can sense her walls going back up, so he decides not to push it. Rather, he rises to his feet and joins her on the chaise, before placing her feet on his lap as he faces her. His lips curl slightly, and the edges of hers begin to slip.

"Maybe that wouldn't be such a bad thing"

 

 

 

**November 7th 2007**

They're both gorgeous, in their own unique way. He can hear the clicks from the phone cameras. Gossip Girl is going to have a field day. He hopes someone will post a video later as well, because that is only going to be good for his reputation. The quickest way to get into a teenage Blair's heart is for him to be accepted by her circle.

"Good Morning Serena" Dan greets, locking gazes with the sunny blonde, feeling the rays of the bright sun on his face.

She looks quite dazzling; Navy scarf wrapped around her neck, covering most the unbuttoning she has done to her white blouse. He doesn't understand why Serena had been so offended when he thought she dressed a tad slutty in high school. But who wouldn't with a body like that.

"Dan" She blinks and her mouth parts slightly open. She wasn't expecting this.

"Can I take you out Friday?" Dan asks confidently.

She smiles at Blair, trying to contain her excitement, but the brunette rolls her eyes, living up to her bitchy persona. Serena stares back at him, worrying her bottom lip.

"I'm sorry to disappoint you Cabbage Patch, but Serena has already made plans to join my sleepover that night" Blair answers for Serena.

That nickname makes him want to barf. He completely forgot about it, thankfully.

"What's your name again?"

Her lips purse, and her face turns into a glower, but it's too darn adorable.

Serena chuckles and places her hand on Blair's thigh, covered with red tights sticking to her skin. "Lighten up B, he's just joking"

"She's right" Dan smirks and sits one step below them, with his body facing their way as he places his messenger bag aside. "Let's make a deal then"

"I don't negotiate with losers" Blair replies, narrowing her eyes at him. "And who said you could sit there?"

He swallows hard, watching Serena arch a brow, challenging him. This is going to be more difficult then he initially imagined. He sucks in a breath and turns his attention back over to Blair, with the minions hanging behind them, backing every bit of attitude the brunette brings.

Oh the minions, how strange their relationship with Blair truly is. He thought slavery was abolished centuries ago.

"Serena still hasn't said no"

Her lips curl just an inch, but that's equivalent to three step forwards when it comes to Blair. "End this poor boy's misery S"

"B" Serena says shyly, as she looks at Blair with her long golden hair casing her face. "I already bailed on him once"

He can't believe it. He never quite understood why Serena was so infatuated with him.

A smirk spreads across his lips as he grabs an apple off from his bag. He takes a bite and chews, soaking in victory.

"So, about that deal"

"Well played Brooklyn" She then glares at Serena before staring back at him. "What do you want?"

"I'm willing to reschedule with Serena if you willing to spare a mattress for my sister" He proposes, before taking another bite out of his apple.

She gasps at his indecency, and tilts her head in the side. "No way"

"Alright then" He rises to his feet, picking up the messenger bag along the way. "I guess I'll see you Friday Serena"

Just when he sets foot on the step below, calling out her bluff, he hears her huff and mumble something inaudible. He stops and turns around, with a smug grin spread across his lips.

"What was that?"

She folds her arms across her chest, staring at him cheekily. "Tell little Humphrey to come find me"

Dan throws his arms out. "See, that wasn't so bad now was it Waldorf?"

Serena laughs and bumps Blair's shoulder playfully, but the feisty girl only offers him a roll of the eyes.

 

 

 

The worst part about being back is re-learning the all the material. Each class feels dreadfully long with some aspects of déjà vu. He sits there staring blankly, waiting for the bell for lunch to ring. At least he knows he has the ability to get into Yale. All he needs is to figure out a way to get the money, and now he has over a year to find a way.

When the class bell finally rings, he takes a breath of relief and gathers his things off the desk. He remembers Chuck would take Nate up on the roof to smoke grass during lunch period. One day, Nate took him up there during senior year and told him it was their secret spot.

He heads over to the old abandoned Lennox building which held all of the science classes prior to the newly constructed Herveaux building. When he arrives to the dark secluded hallway, he hesitates before setting foot into the hall, through the cobwebs. The staircase doesn't appear very reliable, as there are a few nails hanging loose, and the pine railing angled onto the ground now.

After he carefully climbs up the hardwood mahogany brown and white staircase, he turns the golden knob and pushes the door open to see Nate and Chuck standing by the edge, sharing a joint. Nate with his long heroic well kempt hair, and Chuck with his short brown hair pressed to his forehead, projecting his badass demeanor. He on the other hand has always considered him a Carter Baizen wannabe.

"Hey kids" Dan greets.

"You have quite the pair on you" Chuck says, staring at him in disgust; as if he's the most disgraceful human being to ever walk this earth.

What a drama queen. Looking back on it, he considers the whole ordeal childish. He never should have cared about the privileges they had, nor should they have looked down on him for being middle class.

Dan grazes the rim of his left eye, reminding him of the black eye Chuck had once supported. "I thought you knew already"

A crease forms in-between Nate's dark brows, his blue eyes studying him, trying to remember. "Dan right?"

"You didn't check Gossip Girl this morning?" Chuck asks.

Nate blows out a cloud of smoke and hands the joint over to Chuck, staring at Dan. "I don't read that garbage"

"You're such a fucking waste" Chuck shakes his head.

Nate pushes Chuck playfully and turns to Dan. "What are you doing here man?"

"I overheard your conversation with Serena before that brunch" Dan tells him and approaches them, before stopping to form a circle.

"Uh, so?"

"And so he's here to rub it in your face" Chuck concludes with nasty twisty smile of his. "If you don't already know Nathaniel, Serena is dating this insignificant turd"

The kid is just pure evil at this point. He does however accept later in life that Blair was good for him. If it weren't for her, he would have never matured, but that doesn't mean they ever got along.

Dan shoves his hand in the pockets of his slacks and returns Nate's stare, which is blank and lost. He hopes it's the weed.

"That's not why I'm here"

"You need to relax bro" Nate smiles and smacks Chuck in the chest good-naturedly with the back of his hand. "So you were saying you overhead my conversation with Serena"

"Right….It just feels like you clearly have feelings for her"

Nate clears his throat. It appears he caught him by surprise. "Are you sure you're dating Serena?"

It brings a smile to Dan's lips as he stares down to his shoes. Nate never changed, nor did he ever find himself. He's always been one those guys that was good at everything, but never great at one thing.

"Don't worry, I don't have feelings for her" Nate reassures him.

"Dude, I overheard your conversation" He reminds the blonde. "It's obvious you have feelings for her"

The well groomed boy sighs and rubs the back of his head. "Look man, what do you want from me? All I can tell you is that I'm not going after her"

Oh please, he wants to snort, but that would just be too mean. Nate never stood a chance with Serena. It was always in the back of his head they would end up together at some point, but clearly he was mistaken.

"I'm not concerned about you stealing her away from me because I know she doesn't want you. If she did, you'd be dating right now" Dan quips.

Chuck covers his lips with a fisted hand, lifting his brows in surprise. "That's gotta hurt"

"No, I didn't mean it that way" Dan shakes his head and puts his hands up in defense. "I'm not trying to make you feel bad. All I'm saying is that you shouldn't lead Blair on"

Nate lifts his pool blue eyes from the roof top floor, forehead slightly creased. "Why do you care what happens with Blair?"

That's a loaded question. One which he cannot explain to a 16 year old Nate.

"I know this might sound strange" Dan lips curl slightly, as he tries to stop from smiling. "But she opened up to me about her mom recently and I can tell she's going through a tough time…I don't know, I just think leading her on is messed up you know"

Chuck places his hand on Nate's shoulder. "Are you really going to take advice from this leech?" He leans in by Nate's ear, eyes on Dan. "Serena might not realize it, but I do and I'm too smart to fall for it"

With Chuck's meddling, this conversation is going nowhere fast. He has to act quickly or else he'll lose Nate. If he can somehow lessen the blow of their breakup, Blair won't sleep with Chuck for revenge.

"Nate" He calls for his attention. "If you want any future with Blair, you'll break up with her now and explain to her that you need time to figure shit out. Otherwise you're going to keep stringing her along until it blows up in your face and she will never forgive you"

"What are you talking about Humphrey? You don't even know her!" Chuck snaps, nostrils flaring.

"I know that you want to sleep with her" He retorts, taking a step closer towards Chuck, hearing the students out in the courtyard below, enjoying their break. "I know you think about it all the time"

A crease forms between Nate's brows as Chuck swallows hard. "Wait, what?"

"You've know him your entire life man. I dare you to tell me I'm wrong" Dan says, shrugging his shoulders.

"Well this is one fucking jolly lunch" Chuck mutters, flicking the joint aside on the roof tarp.

He takes a step back. "Just remember what I said" He then spins around and leaves them on the roof, hearing Chuck curse him off.

 

 

 

Fuck, that was intense, but scheming has the ability to be unpredictable. The next thing on his list was to speak with his history teacher regarding a timeline project. It's honestly going to be a joke. They're going to be paired up in twos and pick a decade they would like to present to the class, not to mention they'll need to work on a report for the teacher as a part of their grade. He figures it's a way to get Blair alone with him.

He makes sure to get to his teachers office before lunch ends, and so he has to go all the way to other side of the school.

When he arrives in outside the door to Mr. Kimbrel's office, he knocks lightly on the glass door and hears a raspy voice invite him in.

He opens the door and sees the middle aged man, thin gray hair, and long droopy nose. "Hey Mr. Kimbrel"

"Dan" He greets with a smile before tossing his sports illustrated aside on the desk. "What can I do for you?"

"Um" Dan swallows hard and situates himself on the leather chair in front of the desk. "I wanted to go over the timeline project"

"Sure" Mr. Kimbrel leans back on his chair, molding the tips of his fingers against one another. "What do you have in mind?"

"Actually, uh, it's not technically about the project. It's um…It's more about whom I'm going to be paired with" He explains.

"So you have a request" Mr. Kimbrel gathers.

"Right…It's just that I've been paired by teachers before, and it hasn't really worked out for me" He replies. It's not like he's lying. In fact, he wishes he had been more accountable in High School. "Usually, it ends with me doing all the work"

The old man breathes through his nose and studies him for a moment. "Well, I can understand your concern there Mr. Humphrey. It is unfair to place you with someone who will take advantage your academic prominence"

He leans in, meeting his teacher's old tired blue eyes. "I know this is asking a lot, but if you could assign me with Blair Waldorf, I would really appreciate it. She's the only person in class who I know will do her share of the work"

"You know what? You're first in your class so why the hell not. I don't think you deserve to be punished for your hard work"

"Wow, that's great to hear" Dan smiles, feeling much rejoice. "Thank you"

"Anytime" He points his finger to Dan and winks, with a slight click of the tongue. "Don't be a stranger"

 

 

 

The pre-five minute warning bell before class rings and he finds his sister by her locker, grabbing a few of materials for her next class, with students scattering around the hallway.

He leans his shoulder against the cool yellow metal locker and smiles. "Guess who scored you an invitation to Blair Waldorf's sleepover?"

Jenny's eyes widen as she slowly turns her head to meet his eyes. "Dan, I swear to god you better not be joking"

A smug grin spreads across his lips. "I'm not, we made a deal"

His sister suddenly squeals and jumps up and down in excitement, leaving him in a little flustered with the whole hallway staring and all.

"Oh my god" Jenny swallows and clasps her hands together. "Thank you, thank you, thank you!"

"No problem, just don't mess this up, like stabbing her in the back. Follow her lead and she'll take care of you down the road" Dan tells her, hoping she is actually listening to his warning.

Her smile falters and she eyes him suspiciously. "Why do you care what happens to her?"

"I don't" He says lowly, so no one can hear their conversation. Does she not realize Gossip Girl has eyes and ears everywhere? "But I do believe in loyalty. Blair is letting you in, so don't screw it up"

She tugs at her bottom lip for a bit, mulling it over before looking back up at him and nodding.

"I need a favor"

And it's a big one. If he can somehow manage to become best friends with Nate, he can dump Serena. Being Nate Archibald closet ally will give him the opportunity to spend more time around Blair and her circle without leading Serena on.

"Anything" Jenny replies effortlessly.

"How do I become friends with Nate Archibald?" He asks, raising his brows hopefully.

Jenny recoils, appearing a little taken aback by his question. "Err, why would you want to be friends with him?"

"I don't know, I just think he's a really cool guy" Dan explains, cringing internally at his words.

"That doesn't sound anything like you" She notes, staring at him skeptically. "Dan, what's going on with you? You've been acting strange all day"

"Look, I'm human too Jenny. I want have fun and I think having friends wouldn't be such a bad thing" He says.

Her face softens, and he sees the slight guilt in her eyes. What a sucker. He knew she'd fall for that line.

"Okay well, maybe should join the soccer team. Their season will be ending soon, but they start back up in the spring, so it's better to join now and get a grasp of the playbook" She tells him, going in full thinking mode. "Oh, and I know those guys like to play basketball after school out back behind the main Constance building"

"But Jenny, they're not going to want to play with me. Chuck hates me remember" Dan reminds her.

"You have so much to learn" She sighs sadly. "Chuck may hate you, but not everyone else does. You're dating Serena Van Der Woodsen. So be comfortable in your own skin and put yourself out there"

He nods, even though he has a feeling trying to fit in with that crowd is going to be hard. He knows it from watching Jenny do so. But the one thing working on his side this time around is that he knows the Upper East Side inside and out.

 

 

 

He arrives in class, conveniently after Blair. She's sitting in the front row, red headband matching her tights, with her classroom material set meticulously on the desk. He decides to jump on the opportunity to sit right beside her, before some minion, or Blair Waldorf worshipper grabs the empty desk next to her.

Her big brown eyes stay rooted on her phone, as he pulls out the chair and sits down, watching her from the corner of his eye. It's weird. Her shampoo is florescent, with a hint of Chanel No. 5 from her skin, but strangely, he didn't find her scent pleasing until college.

"Hey Blair" Dan greets, waving his hand lamely.

There isn't a guide for getting on Blair's good side. He's watched many try and flounder. It took him four years for her to consider him a friend, so it's not as though he knows the secret of earning her trust. However, he figures he can't wait four years this time around. Otherwise, the results will probably be the same.

She ignores him completely, still engrained in her phone. He supposes it must be an important matter. She does appear slightly furious, but he can't tell if her face is just like that sometimes.

"Did you get a chance to talk to your mom?" He asks.

This gets her attention, leaving his eyes to widen at how quickly her head snaps at his direction. He regrets it immediately.

"You know just because Serena-" She stops and scrunches her nose, staring at his blazer. "Enjoys doing whatever it is you two do, doesn't mean I want your company"

He places the tips of his fingers on his heart, leaning slightly in. "I think we'd get along more than you'd like to admit"

"You?" She challenges, stifling a laugh.

"What's wrong with me?"

He sounds like an insecure girl, but dammit, she makes him feel that way.

"What's right with you?" Blair counters.

He's drawing a blank at this point. Anything he says will make him sound like a stalker. At this point, he's barley supposed to know her.

"I suppose there isn't much" He answers, staring down at his desk, hoping he doesn't sound too down.

"Exactly" Blair agrees. "Now do you mind if I get back to my conversation?"

"No, not at all" He shakes his head.

A fake smile spreads across her lips. "How kind of you"

She turns back, full and undivided attention on her phone, leaving him to lean back on his chair and sigh. Only 1,460 days until they're friends he supposes.


	4. Chapter 4

**Notes for the Chapter:**

> This is a crazy chapter and I believe this will be the last long flashback chapter. Everything else from here is more about the new timeline.

**December 10 2015**

"Did you think about me?"

He swallows hard, staring at her long beautiful curls covering her sharp features; his breathing shallow, and his length pressed against his thigh, begging to be freed upon.

She circles her hips just a little, and it elicits a moan from his lips.

"Of course I did" He tells her.

The tips of her fingers run over his mouth, tugging his bottom lip, sticking to her skin.

"Good" She breathes and presses a soft kiss on the same fingers that were on his lips.

It's turned to night quickly since he last left his girlfriends penthouse, and with one small window in Blair's childhood bedroom, he can barely make her out, except for the glimmering white skin of hers. His other senses however are more aware, like the sound of her breathing, heavy and filled with lust, want, need.

She tilts her head, wetting her full lips, and runs her hands over his chest, molding and digging, letting her choose to fulfill whatever desire she may have.

"I want you" She whispers, leaning down, so that his nose presses up against the cleavage of her dress, thin strap hanging off her shoulder, threatening to fall over.

"Oh god" He groans, turning away as she begins rolling her hips. He catches sight of the time from the digital clock on the ivory bedstand, leaving his eyes to widen.

_Shit, the party._

She grunts, with one final roll of the hips and flips her hair back. "I don't know how I'm going to do this"

"Do what?" He asks softly, the scent of the skin of her cleavage still lingering.

"Stop myself from-" She answers, placing her teeth between her bottom lip, staring at him with those innocent doe eyes of hers. "Having my way with you"

She leans down, and places a chaste kiss on his lips, just before rolling off him.

"Wait, where are you going?"

She's already off the bed, straightening out her dress. "Serena's party, duh"

He tries to sit up, as much as the handcuffs allow. "Well, are you going to uncuff me?"

Oh no, her lips are curling into a devilish smirk. That's never a good sign when it comes to Blair.

"Blair, please don't do this" He pleads. She blows him a kiss, and grabs her purse off the dresser.

"Blair!"

 

 

 

An overwhelming feeling of guilt washes over him.

He doesn't make it home until the sun rises again, wrists sore, and energy sucked out of him. Wary of waking Serena, he thinks better of remaining downstairs, taking in the luxurious home they've made for themselves, the abstract art, high ceilings, and lavish marble floor.

Serena deserves better and he's become her best friend's pathetic lapdog. He considers it to be the ultimate betrayal, something that she can never know because the consequences would be unthinkable. It's the circle of life as Blair likes to say, but he wonders when exactly he had become like them.

He heads towards the kitchen, and grabs leftovers from last evening. His stomach has been growling all morning, so he sits down in the dining room. Blair came back from the party and they had quite the workout.

He chews quietly, with an unsettling feeling, pushing away the voice in his head. It's not like anyone else has a stream of conscious around here.

"Where were you?"

He turns over and lifts his eyes, mouth agape, to see Serena standing by the entrance, in her carnation pink silk robe. Her look is intrepid, filled with slight disgust. Fuck his life; he'd been dreading this moment. Blair left him with very little plausible excuses.

"I am so sorry" He apologizes, dropping the fork aside, expressing deep regret. He wipes his mouth with the table cloth and tosses it aside before pushing himself off the chair.

Serena puts her hand up, leaving him to halt. "Don't"

"I didn't mean for this to happen-I just get in the zone sometimes- you know how it is when I'm hit with a wave of inspiration" He explains.

"You're such a liar!" She cries, and he sees a tear stream down her cheek. Oh my, what did he do? "Do you think I'm stupid?"

He carefully approaches her, keeping his composure. "No, I didn't do anything like that"

She sniffs, still unbelievably beautiful, even with all the gloom. It's just like her. Sometimes he thinks of her beauty as a curse. "Prove it to me then"

"Okay, how? Do you want me to show you what I wrote?"

"You could show me anything and I wouldn't know if it was new!" She whines and stomps her foot.

"Then what would you like me to do?" He asks softly.

She wipes the tears with the back of her hand and sniffs a few more times before meeting his eyes again. "Take off your shirt"

"Babe" Dan tilts his head to the side and smiles. "C'mon, are you serious?"

"Take it off!" She shouts.

His eyes widen, as he can't help but put his hands up, slightly taken aback by her tone. It's so unlike her and it pains him to know he is the one responsible for causing this. It's like he has drained all of her infectious glow, and morphed her into someone he can't recognize.

He takes a breath and nods, slowly unbuttoning his dress shirt, one by one, meeting her sad bleary eyes. His heart beats wildly as he finally undoes the last button. He swallows hard and tugs his shirt off, leaving the scratches, hickeys, and whatever else trail Blair left in full view.

"Oh my god" She sobs and covers her mouth, immediately falling down on the chair. His eyes soften, watching her breaking down in front of him. He can't help but stare away.

"I wish I knew what to say" He whispers.

"I don't understand you" She says weakly, catching his attention.

He licks his dry lips and stares down. "I know"

"I don't feel like I know you anymore" She tells him, as her voice wavers. "This isn't something the Dan I love would do" She huffs out a breath of disbelief and shakes her head. "Blair was right about you. She warned me but I didn't want to believe her"

Maybe she was after all.

 

 

 

Serena kicks him out, rightfully so. Thank god he lives near his father.

He carries his luggage up the old tarnished stairs, one duffle bag slung over his shoulder. The last time he dropped by the loft unexpectedly, he caught Rufus and Ivy sleeping together, basking in the afterglow of sex. Obviously, he's hoping for a different outcome this time around.

"Dan" Rufus smiles, and slides off the stool to meet him halfway.

He drops the duffle bag and throws his arms out. "Looking for a roommate?"

 

 

 

It isn't as bad as he thought it would be. Living with his dad has been a fairly smooth transition. They're both anal about keeping the place spot free, unlike his hoarder of a sister. Not to mention, he's old enough to drink, which is something they can enjoy together now.

"So are you ever going to tell me what happened with Serena?" Rufus asks, placing his bottle of beer on the coaster, by their white rectangular coffee table.

He looks around, taking in the jukebox and guitars plastered on the wall. "You know dad, this is a hipster's dream"

"I guess not" Rufus murmurs.

He chugs his beer, deciding he's going to need another. He can feel his father's eyes on him. Yeah, shit's about to get uncomfortable. So he finishes the bottle and sets it aside.

He wipes his mouth and meets Rufus's eyes, surprised to see how shiny his jet black hair is. It's truly amazing. The man appears to be ageless.

"I messed it up" He says and shrugs his shoulders.

"That's very deep son" Rufus replies wryly.

"Dad!" Dan groans and stares up at the ceiling, praying they don't have to get into this. "It's not something I want to talk about"

"So you'd rather just drink away, and escape from reality until morning comes?" Rufus inquires, brows furrowed in concern. "What good does that do? You'll just have the urge to do the same thing tomorrow"

He hates it when his dad is right.

"Okay" Dan nods in agreement and sighs. "I cheated on Serena"

His father suddenly frowns, unable to mask away his disappointment. "With who?"

He leans his elbows on his thighs and swallows hard. "There was more than one"

It's already suspicious enough the world knows he's written a whole novel about Blair. He doesn't need to leave another trail linking them together.

Rufus sits back on his armchair, slightly appalled. "What happened to you?"

He's getting really tired of hearing that.

 

 

 

"Humphrey"

He sees Blair standing before him, one perfectly sculpted brow arched. She's in a divine black full sleeve twist knot wrap dress, cut slightly in the bottom to tease her long creamy complexion legs. Somehow, they're affair has slipped by Serena and Blair has managed an invitation to her going away party. She volunteered for the Peace Corps and has a twelve month assignment in Africa.

Blair takes a few steps closer and leans in by his ear as he can hear her long golden earrings jiggle. "You haven't called me"

"It goes both ways" Dan replies.

"What game are you playing" She smiles seductively. His knees weaken immediately. The hot whispering leaves his eyes to shut.

"This is the first time I've been outside my loft in a month. It's called depression"

He recently applied to Yale Grad, in the hopes of getting out of New York and spent the past month writing his essay for his application. Fingers crossed, he thinks he has a legitimate shot.

She pulls back, slightly horrified. "You're upset about losing her?"

"She was all I had" He shrugs his shoulders and stares down.

"That's not true at all. I'm going to leave him, but you must give me time. If I divorce him without a plan, I'll lose everything" She says lowly.

He looks up to meet her eyes. "That's too bad, because I'd give up everything to be with you"

Her mouth parts open. She will never be able to conceptualize how much he loves her. At least not until they can date freely, but that doesn't seem to be a reality anymore.

He pinches his lips together and brushes past her to speak with Serena, He finds her surrounded by a circle of friends, an artist, a model, and a photographer. They drink champagne and speak of how much great she will be doing, all the while he stands in the back watching, with his hands shoved in his slacks.

She finally locks gazes with him, and his lips curve slightly.

"Excuse me, I need a moment to speak with Dan" She tells them and smiles, before breaking away and approaching him. She places her hand on her waist and glares. "What are you doing here?"

"I wanted to say goodbye" He answers and lifts his champagne flute.

"Dan, please" She says softly, staring away, with a plead in her voice to make him go away. "You hurt me"

He frowns, seeing her eyes begin to water. "I know and I'm sorry it happened"

There is so much he's learned from their relationship. For one, his realization of how much he doesn't want to be like them. He lost himself in the dangerous feeling of despair and bitterness.

He swallows hard, feeling his face soften. "I'm envious of him"

"Of who?" She asks, brushing her blonde hair aside to meet his eyes.

"Of Chuck" He admits out loud for the first time, watching her mouth fall agape and her face turn to shock. "I want to be over her, but it's not getting any better. It would be a lie for me to say that having a real emotional connection with you is viable"

"Oh Dan" She stares at him, holding a look of pity. "She loves Chuck"

At least she isn't on their trail. He plans on ending whatever it is with Blair as well. Not contacting her for the past month was the first step to his seven step plan of getting over her and moving on with his life.

He reaches for the pocket under his suit jacket and grabs a neatly folded piece of paper.

"I wrote this for you" He tells her and places the piece of paper in her palm. "Please do not read it until you're on the plane"

Mending the platonic side of his relationship with Serena doesn't seem promising. But he did his best, spending the entire night pouring his heart and soul on a piece of paper, hoping she reads it and forgives him one day.

"I hope you can read cursive"

"Ugh, you're such an ass" She rolls her eyes, and he chuckles, hoping to ease some of the tension. She breathes deeply through her nose and places the note carefully in her clutch.

He takes it as progress.

 

 

 

"Humphrey, I didn't' think you'd show"

He pours himself a glass of scotch from their personal bar in the office room of his old home, recognizing the voice as no one other than Chuck Bass. A tired sigh escapes his lips as he turns around to see Chuck, in his three piece double breasted suit.

"Chuck, I didn't expect you to care"

"Well Serena is family after all" Chuck reminds him, practically gloating. "What exactly did you do to drive her away to Africa?"

"If it's not something Serena wants to share, then I'll abide by her wishes to keep it between us"

"Good man" Chuck says and pours himself a glass to join him for a drink. "If you don't want to share, that's fine. Although, you can understand why this news would cause some alarm"

A crease forms in-between his brows.

"Blair, Daniel" Chuck sighs, filling him in on his concern. "I was there to watch you fall in love with her…" He turns his head to meet Dan's eyes. "That type of love doesn't just go away"

"Uh, I think she's made it clear she doesn't want me so my feelings are irrelevant"

"That may be true" Chuck concedes after taking a sip from his drink. "But I must remind you the repercussions if something were to happen"

Oh god, this fucking asshole.

"Like what?"

"For one, I own Waldorf Designs and I have the power to throw Eleanor and her daughter out on the streets" Chuck warns him.

"You've taken some time to think about ways of trapping your wife" Dan deadpans.

He realizes Chuck isn't enthused with his response when he sees the assholes nostrils flaring.

"Thanks for the talk Chuck" He lifts his glass up and walks away, back into the party.

 

 

 

Harold, Blair's father writes a reference letter for him and sends it to the board of admissions of Yale. He gets accepted and his admission begins that fall. He thanks Blair in a personal letter, admitting that he will never know what it feels like to be in love again.

He's become so tired of writing a novel, worrying about little things like grammar and description; he starts working on a screenplay. It's set in high school, based on his experiences and rumors he's heard in the halls of St. Jude's. He originally intended it to be a comedy, but he realized a dark drama piece would be more respected piece of work and he didn't want to be tied to a raunchy high school comedy for the rest of his life.

When summer rolls around, his sister visits the loft once a week, begging him to come outside and not be so fixated on his work. Her concern for him is sweet, but she doesn't understand what it feels like to know that one great love is gone and he will never have that feeling again.

"You know if you would just tell me why you insist on pushing everyone away, maybe I'd understand and stop bugging you" Jenny says, tired of his act.

Long gone is the thick black mascara. She dresses the part of a trendy fashion designer, with some edge. Her hair is less bleach, and more caramel. He likes the look. She doesn't look like a young girl anymore.

He pushes himself away from his work desk and swirls the chair to face her. "I get that you're worried. From afar, it looks like I'm depressed, and lonely, but that's far from the truth"

She arches a brow. "So you're happy?"

His lips curl slightly. "I'm satisfied"

"Dan" She says softly, in such an affectionate manner that it makes him start to feel guilty. "You can't continue to live like this. It's not normal"

"It'll be fine when I start school" He reassures her.

She doesn't buy it and bargains with him until he promises to call Nate back. Too bad he cancelled his phone plan.

 

 

 

He's typing away on his Mac, living in a world with a realm of possibilities when he hears a knock on his window, almost causing him to knock the lit desk lamp over. He rolls his chair back and turns to see Vanessa, kneeled out on the fire escape in the dark. His eyes widen in surprise, but he quickly remembers she's waiting for him to open the window.

He jumps to his feet and lifts the window up.

"Thank you" Vanessa hops into his room, carrying a white plastic bag.

"You're back" Dan says, slightly flabbergasted.

"I brought Indian" She lifts the bag of food slightly up, enticing him. "I hope you're in the mood for something spicy"

"Yeah" Dan shakes his head, still in shock, and gestures her in. "Come in, let me grab some plates"

He leads her to the kitchen, and grabs the plates from the cabinets as she places the food on the table and sits on the sofa, waiting for him. The last time he saw Vanessa, he was upset and said some things he would later regret; the last image being her eyes on the brink of tears.

He joins her on the sofa and sets the plates accordingly.

"Your hair" She notes, and fights a smile from curling. "It's so thick and long"

He chuckles lightly before worrying his lip. "You look exactly the same…Still breathtaking"

She blushes and looks away from him. When did they start being shy around each other? This is his best friend in the world.

"Vanessa, I'm really sorry for letting them push you out of my life" He apologizes, staring at her intently, hoping she knows how genuine he's being.

"It's in the past Dan, I wouldn't be here if I was still upset with you" She says before taking the food out. "Besides, you owe me for getting Inside published"

"Right" Dan smiles easily, feeling a huge weight lifted off his shoulders.

"So" She lifts a brow. "Tell me more about dating Blair Waldorf"

"Of course" Dan rolls his head back, staring up at the ceiling. "I should've known this was coming"

She laughs, and for the first time in a long time, he feels like he can be himself again.

 

 

 

His father leaves to go on tour for the summer, making the loft quieter than before. He has however been going out with Vanessa recently. They went to the poetry festival in Governor's Island, choosing to take the ferry over. Much to her dismay, he elected not to sign up, as he likes to keep his poems close to his chest. They're too personal for him to share over a crowd of a thousand. Rather, he prefers to listen to the artists and be a fan. The best part was going into a dark, mysterious candle lit room after grabbing food from the food truck, and reading poetry one on one with the poet, only to discuss later. It was one of his better days.

They had a few drinks, but he chose to keep the totality of it light before heading back to the ferry. He was hit with a wave of inspiration and didn't want to ruin his thought process.

He comes home, and starts working right away, with the waking hours passing unnoticed. That is until he hears a light polite knock on his door. He checks his watch and realizes he'd been on his Mac for hours and it is now half past midnight.

The first thought that comes to mind is a drunk Vanessa. He smiles and pushes himself away from his work desk to head over through the living room to the front door. Without asking who is at the door, he unlocks it and twists the knob to surprisingly find Blair Waldorf on the other side.

His mouth parts open as he takes her in. She's supporting a summer tan. It's his first tell she just came back to New York. He hasn't been keeping tabs on her, and he's remembering why. She's making him feel all light and fluttery.

Her hair is gorgeous, hidden underneath her red French beret, matching her red lampshade belted mini-skirt with a tight white short sleeve cotton blouse. It's not the usual chestnut brown hair. Instead, it has a light summer shade to it. He loves how everything goes with a season when it comes to her. Each season reminds him of specific version of Blair, and it's nice to think about when he's having a hard day.

From what he can gather, she's having difficulty catching her breath too. He wonders if she feels light headed as well. They stare at each other for what feels like the longest time. He likes looking at her, memorizing each angle of her face and it seems like she enjoys doing the same.

She nervously plays with the ring on her finger, as she keeps locked in his gaze. "Can I come in?"

"I don't know" he says, like he's thinking about it. "It took years getting your scent out of this place"

The ends of her lips barley move, but he can tell she found it amusing. Her eyes appear to darken, and he wants so badly to believe she came here for a reason, and seeing him in person has only elevated her desires.

He steps back and welcomes her in. The familiar sound of heels against his floorboards catches his ears and he closes his eyes, feeling overwhelmed from the memories of them.

"It's been a while" He remarks.

"Would you mind if I sat down?"

He shuts the door and turns around to see her staring at him keenly. He can't recall another time Blair had looked at him the way she is now. Sure, she may have felt the same, but it had never been more obvious.

He can see her pointed heel tugging off the other heel, teasing it on and off her foot. Something tells him she has the itch to kick off her heels and stay for a while.

"No, not at all" Dan gestures over to the sofa. "May I get you something to eat?"

"What do you have on the menu?" She asks, standing by the sofa, holding on to her matching red Prada handbag with both hands.

He takes a breath and lets his eyes fall on her. "I can make anything you want"

"Do you remember those mini cannoli's you used to make?" She chews on her lower lip. "The ones with the caramel pastry cream"

"Oh yeah" Dan stares down and laughs lightly, thinking about the last time he made them. "We'll need to go to the grocery store"

"I don't mind, I have time" She tells him and inches closer.

He tilts his head back up to see her near his proximity, enough to feel the warmth oozing from her sun kissed skin.

"Let's go then"

 

 

 

Thank god the supermarket is open for 24 hours. Although going with Blair was a mistake. She made them grab a cart, even though he found it unnecessary. That was until she started packing his cart with fruits, snacks, and desserts, whatever her little heart desired.

"You're out of control" He says just as she places the golden pound cake on the mountain she has formed in their cart.

She simply rolls her eyes and continues forward with her shopping spree.

"You won't believe what Nina tried to pull"

She stops and swiftly turns around in the aisle, almost crashing with the cart. "What? Tell me"

Jenny's been trying to set her up with a girl she knows in the Waldorf Design's office.

"So she comes to my loft in the morning, with a pair of grey loose sweatpants"

"No" Blair gasps, wide eyed.

"Uh-huh" Dan nods. "And she had the gall to ask me out on a date"

"Oh my god" Blair's mouth falls open. "What did you say?"

"I said, honey, I've tasted caviar, so why don't you hit the road" Dan gestures back with his thumb.

"You did" Blair's browns grew in excitement.

"Yes, I said no to her because she chose to wear sweatpants" He says dryly.

She pouts her lips. "Humphrey, that wasn't funny"

"It was to me" He chuckles and continues on pushing the cart.

She presses her lips tightly and glares before moving onward.

"You know Penelope referred me over the south beach diet via email?"

"She didn't"

"Yeah" Blair nods. "And she cc'd everyone on the email"

"That bitch" He says, shaking his head in disgust.

"Exactly Humphrey, exactly"

"Well you look amazing to me" He admires the swaying of her hips.

"That's because I just shed fifteen pounds" She murmurs.

"Blair" He tilts his head to the side, brows furrowed in concern.

She puts her hand up to refrain him from saying any more. "Humphrey please, not here"

He nods and continues following her through the aisle.

They spend an hour in the supermarket, and all time personal record for him. He's realized Blair is one expensive girl to date. She offers to pay, but luckily he has his career in order and declines her offer.

Much to his dismay, they take a cab back to the loft, because Blair Waldorf doesn't carry grocery bags. He's starting to pick up on why it's better for Dorota to buy the groceries after all.

 

 

 

"You're good at that" Blair says, leaning over his counter, and watching him wrap the cannoli's before placing it on the parchment paper on the baking tray.

"Nate taught me well"

Her eyes light up. "You smoked?"

"There was a period in college-" He admits and finishes rolling the last cannoli. "I suppose you could call it a phase"

"I never knew that" She pouts her lips. "Why didn't you guys call me?"

"Blair, can we not go down this road?" Dan pleads, placing the baking tray in the oven.

"Daaaan" She whines, and he tilts his head to the side. She knows he hates it when she stretches his name to get what she wants.

He wipes his fingers with the hand towel and turns around to face her, with the kitchen island between them.

"Because you were so busy trying to make things with Chuck work, that you forgot to enjoy college"

"Oh" Her eyes cast down.

"Yeah" He says, feeling sad for her.

In one blink of an eye, she was married, and running a multinational fashion company before the age of 22. He does appreciate not being stuck on Serena after high school. Thankfully, he dated around and had the opportunity of experiencing all that was great with college, unlike her, who was miserable at NYU, and heartbroken for the latter.

She lifts her eyes to meet his. "I wish I could go back"

"That would be awesome" He replies, earning him a small laugh.

"What would you do differently?" She inquires, eyes filled with curiosity.

"I think the only thing that I really regret is the way I handled our breakup, and that's only because those decisions were out of character for me" He answers truthfully.

"Ha" She leans back off the wooden counter and arches a brow. "What about Ms. Carr?"

"I don't regret that" He says, smiling amusedly. "That was fun"

She folds her arms across her chest and narrows her eyes at him. "Well lucky you"

"I'm going to go wash my hands, but please, continue to be a baby" He smirks and heads for the bathroom.

He turns on the faucet and stares at the mirror to wash away anything that may have reached his face, humming away.

"You know what I regret?"

He stops washing abruptly and turns to see her standing by the doorway. "I have an idea"

She walks toward him with lithe accenting every movement of her body. His eyes fall victim to her ways of seduction. When she wraps her arms around his neck, he stares down at her lips, knowing how much selfish it is to have his way with her. But he leans in anyway, because he can't resist the best feeling in the world.

 

 

 

**September 8, 2032**

His divorce was finalized and he was expecting a call from his lawyer, congratulating him, but when the phone rang, it turned out to be Nate, with some bad news.

He steps into the room, filled with black, and walks down the narrow aisle, all the way down to the large open casket. He hears his name called, but he continues, wanting to know if it really is true. It doesn't make any sense.

When he reaches the casket, he peers over and sees her beautiful fox like face, chestnut hair brushed, and perfectly sculpted eyebrows.


	5. Chapter 5

The soccer coach advises him to borrow spare soccer gear from a teammate before practice, not realizing the kid from Brooklyn isn't fortunate enough to have any friends. That leaves him with Serena, the only person who would ever consider helping him.

He stalks the Constance Billiard halls in between periods until he finds the leggy blonde by her locker, stuffing a geography book in her leather bag.

"Serena" He calls.

She slams her locker shut and looks over. A wide alluring smile spreads across her lips.

"Hey!" She waves her hand, full of glow and excitement. "What brings you here?"

"Well um" He clasps his hands together and approaches her. "I joined the soccer team today"

"Oh, good for you"

"Thanks, but I've run into a problem" He tells her, squinting his eyes in worry. "See I don't have any soccer gear and I don't how I could possibly get some by practice. Would you by any chance know anyone who wouldn't mind lending there spare gear?"

"You know what, better yet, let me call my mother's assistant" She replies nonchalantly, likes it no big deal at all.

"Really?" He asks, voice filled with hope.

"Yeah, meet me outside the boy's locker room after school" She winks and begins walking around him to head for class. "Ta-ta Dan"

He lets out a breath of disbelief, as he turns around to watch her head down the hallway. Well that was easy.

  
  
  
  
  


Loud chatter fills the small stuffed narrow hall, as he waits with the rest of the soccer team for coach to unlock the locker room. Everyone knows one another, and he still feels insecure about his place amongst the group of boys. He places his headphones in his ear and leans his shoulder against the wall, avoiding all eye contact.

Nate stands up in the front, with the seniors, laughing and reminiscing about their trip to states the year before. It seems hard to picture being in their circle now, but he figures his play will ease the transition. He's always been good at soccer and it's one of the reasons he was able to form a friendship with Nate in the first place.

When everyone stops talking to stare behind him, his brows furrow in confusion. The mystery unveils itself when he takes the ear bud off and looks over his shoulder to see Serena clicking her heels over to him, blouse untucked, and tie loosened, like a girl who doesn't live by the rules. She's carrying a bag, just for him. What a life-saver.

"Look what I have" She sings, shaking the bag in front of him.

Dan pushes himself off the wall and turns around fully. "Oh my god, you are awesome"

"I know" She shrugs, holding a smile, knowing it's absolutely true.

She hands him the bag, and he looks inside to see cleats, shorts, and multiple shin guards. It would be such a small problem for someone normal, and if it were any other girl, she would be off put by his zero friends. But Serena is never one to judge or care.

"I owe you so much" He can't help but say.

"Well, you have Saturday night to thank me" She reminds him.

"It will be the best date you've ever had" He says, knowing her love of mopeds. Serena's always been easy.

"I'm going to hold you to that"

She leans in and presses a soft kiss by the corner of his lip. His cheeks flushes as he can feel the hole growing deeper and deeper. Serena is falling for him, making their inevitable break up more difficult. He doesn't know how he's going to do it, but that's something he can worry about another day.

When she pulls away, she offers him a sly smile before spinning around to head down the hallway. He swallows hard and goes back to face the locker room, only to see the entire team staring at him.

"Good for you Brooklyn" One of the boys says.

"Even Baizen couldn't tap that!" a Senior shouts.

He shakes his head and places the ear bud back in, waiting on the coach.

  
  
  
  
  


So he was wrong about impressing them with his soccer talents. Even though he has the skills to play soccer, he forgot one important variable. He's completely out of shape.

After stretching, the first item on hand for practice is running laps around the field. Unfortunately, by the time their done, he's running by the fence, and throwing up the BLT sandwich he had for lunch, with everyone laughing at him.

However, he does fine in the drills, impressing them with his leg and above average dribbling skills. But when they start the scrimmage, he's worn out by the end and isn't able to keep up with his teammates. The only highlight of the practice is him landing hard on the grass after a good solid tackle, and Nate coming over to help him up with a large grin on his face.

  
  
  
  
  


He takes the public bus back home, and when he finally arrives to the loft, he immediately plants his face on his bed, crying in pain against the bed sheet.

"I take it practice didn't go so well"

He rolls over and props himself up with his elbows to see his sister by the doorway. "It was humiliating"

"It'll get better" She assures him.

"How do you get them to like you?"

"Who says they like me?" Jenny steps into his room and takes a seat on his desk chair.

He grimaces from the soreness as he readjusts himself to sit on the edge of the bed. "Blair would never have agreed to my demands if she wasn't already thinking about it"

Jenny looks down to hide her smile. He totally gets why his sister is obsessed with being one of them. In fact, he's always wanted to know what it was like himself. His curiosity began when he managed to sneak into that party Blair threw their freshman year.

"I don't know. It's harder with girls" She stares back up. "They're materialistic and shallow, but um, I've been able to impress them with the clothes I design and my understanding of how the social hierarchy works"

"It's hard for me" He shakes his head. "People like Blair call me a charity case all the time"

"You have to ignore it and find a way to fit in" She explains.

He falls on his back and groans, rubbing his face with both hands. "This is going to be so hard"

  
  
  
  
  


He's trying to finish his homework when he hears the argument outside his door, between his father and Jenny. His father's discipline had become a disaster, but thankfully, his sister was able to get her shit together after living with their mother.

One his deeper regret was not being there for Jenny. Looking back on it now, he blames himself for the way things transpired in high school, even though there were times where she took it too far and displayed her immaturity. The popularity got to her head, and trying to get in the way will only push her away in the end.

When he opens the door, he sees Jenny breathing long and hard, fingers curled in fists as his father stands calmly, with his arms folded across his chest.

"You should let her go" Dan chimes in.

Rufus puts his hand up to stop him from saying anymore. "I'm not going to change my mind on this"

"Dad, you made the decision of having us go here and now we're the ones who have to deal with the repercussions. If you don't allow Jenny to be in equal foot with the rest of the girls in her class, well then it's going to be hard for her to make friends" He says.

"Right son, but-"

"And, at least Jenny is telling you the truth and not hiding the circumstances of the situation, but if you keep pushing her, she's only going to start lying to you" Dan cuts him off.

Jenny looks at him, with great appreciation and mouths thank you.

"So what? I should just let her go to this sleepover and become influenced by spoiled young girls?" Rufus asks.

"Being them isn't such a bad thing. As long as she's able to maintain her grades, I don't see why you can't trust her"

Rufus takes a breath and looks away for a moment to think.

"Okay" He sighs in defeat.

"Yes!" Jenny jumps up and down.

"Dan" Rufus glances over to him and waggles his finger at him, warning him. "You know everything that is going on with school and her friends. So I'm holding you responsible for her. Do you understand?"

He nods, accepting the burden of his sister rebellious behavior.

"Okay, I'm heading out, don't wait up for me" Rufus tells them and grabs his jacket from the coat rack. "Remember, it's a school night"

His father opens the door and recoils in surprise to find a girl on the other side.

Dan's mouth parts open when he recognizes Serena Van Der Woodsen standing there, in a tight striped crew neck sweater and denim jeans. What is she doing at his place? Their date isn't until Saturday and he doesn't remember her ever coming over in-between the days.

"Hi, I'm Serena" She greets.

"It's nice to finally meet you. The name's Rufus, and you can thank me for his looks"

Dan groans, and smacks his forehead, shaking his head in embarrassment. Of course Serena just laughs and steps into the loft.

"Hi Dan" She says shyly, only for him to see his father putting two thumbs up as he stands behind her.

Dan rolls his eyes and grabs Serena's hand to save himself from any further embarrassment. He leads them to his bedroom. Luckily, he has a habit of keeping it clean.

"So, this is my room"

Serena looks around, and he stands behind her, watching her take everything in.

"It's nice" She says softly.

"Uh, thanks" Dan rubs the back of his head nervously. "Is there something I can get for you, water maybe?"

"I'm okay, thank you" She answers cordially, and continues to stare around his room. "I came by to see how practice went"

He stuffs his hands in his pockets, as the speaker dock plays a song from The Helio Sequence in the background. That really does take him back. Boy did he ever miss having the time to simply lie on his bed, and soak in the music filled on his mp3 player. It's hard to remember why he never lived more in the moment. He was so focused on holding a grudge for not have the same advantages that he never appreciated everything in front of him.

"You have good taste in music" Serena says, staring at his black speaker dock.

"Really?" A crease forms in-between his brows. "I thought you'd enjoy something with more pop"

"I like" She pauses to take a deep tired breath and glances over to him. "I'm not always so happy"

He nods, knowing full well she isn't, but everyone only sees one thing; a sunny blonde with a matching smile.

"You mean like what happened with Nate"

She stares away. "That's one instance, sure"

"Why did you do it, if you don't mind me asking?"

Her eyes widen, and she looks like she wants to run away. No one ever challenges her because she's always been number one. And so he's not surprised to see why she reacted the she did when he wanted Blair.

He settles against his study desk, and folds his arms across his chest, waiting for her to say something.

"I don't know the reason" She answers finally, after deep thought.

"Did you love him?"

"I've never been in love with anyone before" She says with no hesitance.

"Then why?"

"Why does it matter?" She asks back, meeting his eyes.

"I just want to understand you" He explains, eyes softening.

She sighs and falls on his bed, staring up at the ceiling. She's going to be here for a while he presumes. He supposes Upper East Siders aren't concerned with school nights. It's too bad; he was hoping he could get some writing done.

"He was something I couldn't have" She confesses.

That's what makes her such a train-wreck. He should've known what she was when they started dating, but he was too enamored with the idea of being with his dream girl.

"Does that make me a terrible person?"

"It does to Blair" Dan answers, shrugging his shoulders.

"Ugh" She groans and covers her face with both hands. "I don't deserve her"

"How do you go back to being friends after that?" He inquires.

That's always something that has bothered him about them. It's as though like Blair has decided to erase the betrayal of the two people who she trusted more than any other, and pretend everything is okay.

"We just to do"

He joins her on the bed and turns his head to stare at her. "It's never that simple"

"Well let's hope you're wrong" She meets his eyes, and smiles.

Lying in bed with her isn't his ideal situation. Many things can happen, for one Serena wanting a kiss. How is he exactly supposed to say no? All he can do is act his ass off until she eases him into her circle.

"You know Nate is in love with you" Her eyes peer down, straying away from his gaze. "And yet you keep pushing him on Blair"

"They belong together" She lifts her eyes back to him.

"I think you want everything to be back to the way it was because you feel guilty"

She props herself up with one elbow, body still facing him. "Why are you pushing this?"

Maybe he's being inconsiderate, but what does he really have to lose. The two girls need to resolve their issues for Blair to be happy. Otherwise, they will continue on with the venomous cycle of fighting for attention and stabbing one another's back.

"Hey, there's no need for you to be offended" He puts his hands up in defense and smirks.

She narrows her eyes, staring at him suspiciously. "Since when do you care about Blair?"

"She's your best friend, of course I care" Dan explains and places his hand on her arm. Her body shivers, and he can see her breath being taken away by his touch. He sees everything so differently now.

Serena lies on her back, shutting her eyes and taking a couple of deep breaths to relax. "You're such a good guy"

"You don't know me well enough to say that"

Her eyes open and fall on his lips, as the tips of her fingers graze his jawline. "I think I do"

This is the moment he is supposed to kiss her, and rock her short-minded teenage world. He doesn't necessarily want to kiss her, but he fears the consequences of pushing Serena out of his life. He really needs to get that Nate plan in place.

  
  
  
  
  


The next morning, he wakes up and finds the other side of his bed empty. No note or message on his phone, just vintage Serena.

He skips breakfast and heads straight for the MET steps to find Blair, Serena, and the minions, including his sister unfortunately. She should be better than this, but it's what she wants, so he can only accept fate for what it is.

"Do you guys mind if I join you," He asks, locking gazes with a blushing Serena. His eyes drift down to see her grasping onto Blair's arm.

"Yes, we do" Blair scrunches her face. "I heard the band is looking for a flute player"

The girls laugh, including Jenny much to his disappointment. However Serena glares at Blair, leaving the rest to settle down. He honestly doesn't care. The chance to breathe the same air as Blair Waldorf is enough for him. He can sense all the pain she is hiding underneath that confident haughty tone of hers. All he wants to do is heal it and make sure nobody ever hurts her again, even if it's going to take her years to get over this spoiled brat stage of her life. He can deal with it, because he knows what she's capable of being.

Blair rolls her eyes. "Oh fine, come hither Humphrey"

"You can call me Dan you know" He tells her, lifting his messenger bag over his head, and sitting a step below them.

"Or how about cabbage patch?" She proposes. "I think that suits you much better don't you think?"

He sighs and shakes his head. "I don't understand what I did to you"

"Everything about you is offensive, from your wardrobe to your hair"

His jaw clenches tightly as he stares straight into her eyes. This is not going the way he wants at all, and she's really starting to piss him off.

"Blair!" Serena scolds.

"You know, I may not have the resources you do, but I can confidently say that I'm happy. So you can keep taking a shit on me and feel better about yourself" Dan retorts, leaving her mouth to part open in surprise.

He grabs his messenger bag and rises to his feet, shaking his head as he storms down the steps.

  
  
  
  
  


He slams the locker shut, still steaming from earlier in the morning. It's going to be impossible dealing with her. He forgot how unreasonable she was.

"Whoa there" Nate puts his hand up, carrying a grin. "Everything alright?"

"Yeah, I'm fine" He stuffs his bag with a notebook and glances over. "Is there something you need?"

"Well um, I just wanted thank you," Nate says, shoving his hands down his slacks. "I took your advice"

A crease forms in-between his brows. "What?"

"Yeah man, I opened up and told her everything last night" Nate tells him.

"How did she react?"

Nate licks his lips and smirks. "She said she'd wait for me"

He lets out a breath of disbelief and stops himself from shaking his head. "That's good to hear"

"I owe you one"

"You just let Blair Waldorf free to flirt with whoever her little heart desires, let's see how long you'll be thanking me" He jokes, earning him a light chuckle from Nate.

  
  
  
  
  


Blair's attitude towards him in the morning makes much more sense and his frustration with her starts to dissipate. Now, all he can think about is a making her day a little brighter. He doesn't know how he's going to be able to deal with the rollercoaster ride of teenage emotions. His heart was much softer as he aged, but now, he has all this anger built up and he can't understand why. He hates having to carry these raging hormones.

The class bell rings, ending another class session, leaving the students to rush out of the classroom for lunch. He heads for the cafeteria, and groans when he sees the wide assortment of stale pizza. Luckily, he's in private school, and they have a fresh grill menu.

He ends up sitting alone, with everyone soaked in their bubble of conversations, leaving him with the feeling of being left out. He frowns and stabs at his grilled vegetables.

"Hey Dan"

He lifts his eyes to see Serena placing her bag on the table as she settles in to join him. She takes a spoonful of her yogurt and giggles when she sees him staring.

"Last night was fun"

"Sure" Dan nods, hearing clicks from the pictures being taken.

She leans in. "Can I let you in on a little secret?"

"Of course" His lips curve slightly.

"That was the best kiss I've ever had" She tells him and lets her eyes fall away from him.

He smiles. "Same for me"

She looks back up, eyes wide in excitement. "Honestly, I wish I didn't have to go to that sleepover so we could go out today"

"It's fine, Blair needs you more than ever anyway"

"You're right" She shuts her eyes and shakes her head. "I can't believe Nate used her like that" She then stares at him in slight awe. "I never should've pushed them together"

"You thought it was what Blair wanted" He reasons.

"Thanks Dan, but you don't have to make me feel better" She says and takes another spoonful.

"No MET steps today?" Nate asks, placing his tray of food on the table to join them.

"No" Her blue eyes go to Dan before falling back on Nate. "I like having lunch with Dan"

And just like that, his table starts filling one by one, as they greet Serena and join them, like it's any other day. No one says anything snide, they just sit down, and add to the conversation.

  
  
  
  
  


He spends his entire Friday night writing a short story he has already written in his other life. One way to collect enough money to pay for Yale is selling off his writing talent.

Saturday comes quicker than he anticipates, and before he knows it, he's in Serena's penthouse, waiting for her in the extravagant living room.

"Can I help you?"

He looks across to see Lily Van Der Woodsen, blonde hair tied in a bun.

"Oh um, hi I'm Dan" He jumps to his feet and sticks his hand out to greet her. "I'm taking Serena out on a date"

"I see" She narrows her eyes. "My daughter doesn't discuss her life with me, so excuse me if I come across as surprised"

"Right"

"Well, I'll let you get to it then" Lily says before turning around.

"My dad says hi by the way"

She stops abruptly and turns around to get a good look at him. "What did you say your name was again?"

"Dan Humphrey," He states and approaches her.

She smiles in disbelief, unable to accept the reality of the situation. "Of course"

"Life's funny isn't it?"

Her eyes flicker over to him. "Good luck with my daughter Daniel"

He nods, and she walks away, lost in deep thought, probably reminiscing in the past.

  
  
  
  
  


When Sunday arrives, he finds himself in familiar territory. After taking Serena on a ride around the city in a moped, they ended the night with a rock show, before hitting the sack, knowing Blair would be waiting for him the next day.

The elevator opens, and he sets foot in Blair's foyer. He takes a moment to look around, at all the paintings and family pictures.

"Ms. Blair waiting upstairs"

He spins around to see the warm Dorota, eyeing him suspiciously.

"I don't believe we've met. I'm Dan by the way" He greets.

"Ms. Blair only allow me to call you lowly boy"

"Good to know" He chuckles.

"Follow me" She tells him, as the hefty maid leads him up the staircase.

They head down a wide hallway, with large frame paintings, and plush carpeting until they reach the library, where he finds Blair sitting by a desk, eyes focused on the laptop screen. It appears as though she has already begun working on their project.

"Lowly Boy is here" Dorota announces.

Blair's doe eyes lift up to him. "Leave us"

The maid suddenly scurries away, leaving him slightly confused.

She leans back in her chair, folding her arms across her chest. "Humphrey, you're late"

He rubs the back of his head. "Sorry to keep you waiting, hard to predict the subway sometimes"

She presses her perfect bow shaped glossed lips in displeasure. His heart is about to explode. He can't believe he is here, with her, all alone. She has a ridiculous headband on. It's tied in a bow, and matches her long sleeve fair weather navy blue sweater dress. And he loves it.

"Whatever, I started without you" She sighs tiredly. "I found a bunch of links we can refer to as sources. I emailed them to you. If you could read through them and write notes on anything you deem important, that would be helpful"

"Of course, thanks for doing that" He says, in awe of her organization and determination.

She slides over a spare laptop next to her. "Here, you can use this"

"That's okay, I brought my own"

"I didn't know they had computers in Brooklyn" Blair murmurs, leaving him shake his head before taking a seat next to her.

They start working on their separate tasks, and every so often, he watches her work. He loves the way her brows remain in deep rooted concentration, or how she chews on her lip when she's unsure. Then there is how amazing she smells, like swimming in water filled of roses.

"What?" She stares at him incredulously when she catches him staring.

"Nothing" his eyes fall back on the laptop, away from her.

"Why do you keep staring at me?"

"It's just-" He stops himself, knowing he is going to make a fool of himself if he says anything further.

"Oh just spill it already" She replies.

"You're really pretty" He says quietly, shutting his eyes, and not daring to look at her.

He wishes he had a better control of his emotions, but this teenager thing is really killing him.

"Ugh, shut up" She rolls her eyes.

He would feel like shit, but when he looks over, with the corner of his eyes, he catches her smiling as she continues to work.


	6. Chapter 6

No one is able to see through the Ice Queen facade.

Gossip Girl framed her break up with Nate as beneficial for both parties. It was the talk of the halls for a week, everyone contemplating what was next for the two. Although, his concern solely lied with her broken heart.

That's how he came up with the concept of an secret admirer. He has since been excusing himself for the bathroom in the middle of class periods so that he can slip a folded hand written love note into her locker.

He writes silly things, like his thoughts on her recent political decisions leading to social annihilation or describing her choice in wear and how it compliments her skin.

There had not been any signs of progress over the following weeks, until Katie and Is shared a rumor with him the other day, on the MET Steps in the morning while Queen B was unable to make it due to a dentist appointment. They have a inkling something or someone has been distracting Blair.

"What makes you say that," Dan asks, staring down at the sitting girls.

"We caught her singing," Kati says before both girls turn to each other to giggle amongst themselves.

Apparently, they were heading up the staircase, and caught Blair brushing her hair and singing through the door ajar. He figures she's thinking about Nate, but he can't help but have little hope his words brought the smile to her face.

  
  
  


He stops making visits to the MET steps in the morning. It ultimately saves him thirty minutes for extra sleep. He sees Serena enough during the day and would prefer not to sit there to watch Blair moon over Nate.

"Humphrey, you better not squeal," Blair whispers harshly before slamming her books down on the table to join him in the library during lunch period.

His plan for Nate confronting Blair didn't go so well. She sought revenge and made out with Chuck in a bedroom during a party. When Nate caught the two, he punched Chuck square in the jaw. However, Nate has no idea the entire thing was set up by Blair, with a little help from Serena pushing Nate to go look for Blair. The only reason he knows this is because Serena shared it with him, while the two were having dinner at Bart's.

He lifts his eyes away from the book. "Not now, I'm trying to study here."

She glares at him for a brief moment before taking a seat next to him anyway. Her pink glossy lips then puff into a pout. "You've been very sour lately. It's no fun when there isn't any tit for tat."

He sees her staring his way, giving him her full and undivided attention in her white collared full sleeve blouse. All this time he's been searching for a way to squeeze into her thoughts, not knowing ignoring her would get him this far. She has set such a bad precedent for herself, it's hard to remain upset with her.

"I'm not hired entertainment Waldorf."

His attention falls back on his book. He's in the middle of an example, not that she would give one shit.

Her incessant tapping of fingers against the wood of the table however starts becoming distracting, enough for him to peel his eyes off mid sentence.

Sure, he could push the book aside and spend the entire lunch period trying to win over Blair Waldorf's heart, but that isn't him. He wasn't a failure before, and he isn't going to be a failure in this life.

"Alright, what do you want," He asks, shutting his book and leaning back into the chair.

"Why do you think I want something," She challenges.

He rolls his eyes, growing tired of her wall. "Just get to the point Waldorf."

She appears slightly taken aback by his direct approach, but decides to pursue anyway. "So Nate and I had a huge argument last night as you probably saw on Gossip Girl."

"That's unexpected," He adds dryly.

Her eyes narrow. "Anyways, Serena said you could help."

"You know you can't will him to be in love with you right?"

"I'm not-" She then presses her lips together and shakes her head. "That's not what I'm asking from you."

He leans in, curious of what is going through her head. "What can I help you with?"

She straightens out her headband and gives an airy sniff, reminding him that she is still Blair Waldorf and he is nothing more than a insignificant piece of turd.

"Do you know what Vanessa wants with Nate?"

Vanessa came back on a random Saturday morning and has yet to share her feelings with him. He's been waiting for the words to come out, but he thinks he may have already altered the timeline slightly.

"Nothing," He answers.

She tilts her head to the side, staring at him questionably. "Do you seriously expect me to believe that?"

He licks his lips and meets her eyes. "We have history."

She lifts a perfectly sculpted eyebrow, and gives him a dubious stare, like why in the world would two pretty girls be into him.

He realizes how close they are to each other and his breath shortens. Her skin oozes of warmth, drawing him closer. She smells amazing; high end perfume mixed in with lily in the valley hair shampoo. It goes all the way up to his brain cells, making his sight fuzzy.

"A couple of years ago, I told her I loved her."

Her eyes fall on his lips before going back up to his eyes.

He tries so hard not to stare down at her chest, not that she would notice the effect she is having on him.

He swallows hard. "And she ran away."

Her lips start to curve as she attempts to suppress her laughter, that is until she gives in and covers her mouth with her hand. She's shaking, body slumped over, leaving him full of humiliation. He simply turns his attention back to his book, ignoring her immaturity.

"Wow, I never thought I would have something in common with Vanessa," She teases, in a fit of giggles. "I would check the deadlines for boarding schools before sharing those words with Serena."

This conversation is turning into a disaster.

"Yes, what could Serena possibly see in me," Dan ponders out loud, voice reeking of dry sarcasm.

"I don't know, but I hired her a therapist," Blair says.

"I'm-I'm not-"

His stuttering is pathetic.

"Look," He gathers himself after being completely humiliated. "I'm not that bad."

"Humphrey," She stares at him in pity. "You're not even in the field of vision."

He frowns, disappointed in his inability to get past her defense mechanisms.

She's seems to be enjoying herself on the other hand, with her superior smile and look of satisfaction. Their relationship is impossible to grasp.

  
  
  


Thanksgiving passes, and strangely, the loft is crammed. His mother surprised them the other morning, and Rufus became overcome with false hope of his family being whole once again.

Everything has panned out the way it did before, except with Blair remaining a virgin, and Vanessa not coming to him with her feelings.

The ongoing tension between them comes out one day, when they're coming back to the loft after one of his father's shows.

"Are you in love with Serena?"

"What?" Dan appears startled as they set foot in the living room. "Where is this coming from?"

"You've been spending a lot of time with me," She points out, giving him the time to _cut the bullshit with me_ Dan look. "That usually doesn't bode well."

"Well." He sighs and sits on the stool. "I don't know how to say this, but in terms of technically, I'm not really that into Serena."

Her mouth parts open in surprise, as a crease forms in-between her brows. "Are you for real?"

"It gets worse." His brows furrow in worry of her reaction. "I'm only doing it because it gives me the opportunity to talk to Blair."

She places her hand on her forehead and stares at him incredulously. "Dan, what are you talking about?"

"Serena's my way in." He shrugs his shoulders.

She huffs out a breath of disbelief and turns sharply away, running her fingers through her curly raven hair.

"I'm only telling you this because you're my best friend and I want to be able to share this with someone," He tries to explain, standing up and approaching her warily.

"Your being manipulative," She says, holding her urge to scream at him.

"I've done nothing to manipulate Blair into falling for me. I've only been myself, and I'm hoping that'll be enough."

"It won't be." She shakes her head, looking at him in slight disgust before heading for the door.

He throws his hands up in surprise. "Where are you going?"

"I can't be around you right now," She replies, and slams the door shut.

His shoulders fall as he stares down, slumping.

  
  
  


Every morning, he comes to school, and spots Blair sitting on the MET Steps, away from the girls, staring down and reading one of his handwritten letters. Her smile is a reserved, an act for the people staring, but he can feel her happiness threatening to burst for all eyes to witness.

"What a bitch."

He glances over to see his sister shaking her head in disapproval, with her cute school colored snow hat staying in place.

Blair made her cry the other day, after giving her impossible tasks, like waking her up at three in the morning to paint the queens toenails. There was also the time Blair made Jenny take the blame for passing notes in class. But that hurdle to overcome is for another day.

"I can't do this anymore," Jenny says exasperatedly.

"It'll get better," He reassures, staring at the brunette reading.

The December weather has impaired most to remain inside, exception being Queen B and her crew of girls. He takes a sip from his warm coffee; black, no sugar, and moves towards the top of the steps.

His cheeks blush slightly from the frosty wind chill hitting his face. Blair seems cozy, by her lonesome. She's in a navy blue double breasted military jacket, matching her school uniform and tie, not showing him a lick of displeasure from the frigid air.

"Morning Blair," He greets, lips curling into a smile.

She lifts her eyes off the crumply hand-written letter, to stare at him from toe to head, with a conceited smile that he finds just so god dam sexy. His dick would always manage to jump at the sight of her devious stare. It's much different from Serena. Blair appears up tight, but the bad girl in her has always been irresistible.

Her brow arches. "What brings you here?"

"You've been mean to Jenny," He says, noting the bright hot pink folder stuffed with his notes.

"I can't be nice to her. What would people say?"

He chuckles and takes a seat next to her, watching her raise both eyebrows in surprise. He leans in, just brushing his shoulder next to hers.

"I'm not here to fight my sister's battles."

"Then what are you here for," She asks.

Thank the lord. It took months of persistence, but Blair Waldorf is finally having a normal conversation with him.

"I'm sure you've heard." Dan smirks.

"Oh yes, you're joining S and I," She recalls, thinking back on their dinner plans tonight.

"Is she upset with me?"

She stares at him, dumbfounded. "Humphrey, of course she's upset with you. Girls want to be courted. We're starving for attention and like every typical guy, something else has caught yours."

Serena keeps pushing them towards a more physical relationship. He had to go down on her the last time they were together, alone.

"How much has she told you?"

"Enough to know you've been around," She's says, holding a wicked grin. She leans closer, just so only he can hear. "So why are you hiding from Serena?"

His eyes soften and fall into disappointment as they hold gaze. "I don't know how to explain it."

"There's nothing to explain." She rolls her eyes and shifts into best friend protection mode. "Serena is gorgeous and you clearly seek help for not taking it to the next level."

"First, don't get snippy with me," She narrows her eyes, but it comes off as playful. "Second, I would prefer to have sex with someone I'm in love with."

Her mouth falls slightly ajar, taken afar by his words. She pushed him until only the truth remain, a classic Blair Waldorf tactic.

"How can you not be in love with her? Haven't you been stalking her for years?"

"I'm not lying about my feelings." He rolls his eyes, throwing it back at her. She can be exhausting.

She stays quiet after, and he is gifted with the opportunity to stare at her long enough to see her chest pound in and out. Her eyes are entrenched on the letter in her hand.

She swipes a thumb over a word he can't make out. He's already written so many, he can't recollect the exact one. After a while, he decided to slip a neatly folded letter into her locker on Fridays only.

The anticipation of today's letter must be wavering in her thoughts.

His brain is clashing with his hormones and clouding his judgement. Suddenly, he feels guilty for taking advantage of her. She's been scorned recently, and left vulnerable. Yet, there is no other purpose of being here.

He doesn't know why he has been re-born into this body. He recalls dying peacefully in his sleep. And now, he woke up into this, knowing all the details of his life, but fighting nonsensical teenage hormones.

  
  
  


There is nobody more excited hearing the bell ring than him. He's helping his father set up the band equipment for Lincoln Hawk's concert and then meeting Serena and Blair for dinner.

Blair will murder him if he's late.

Luckily, there is a narrow passage through the halls this afternoon. Everyone is going on their last runs to see if they received an invitation for Kelly Musker's party. She's a senior and her parents are out of the country; vacationing in Saint Tropez he last heard.

Serena already received her invitation and he could sense the tension between her and Blair during lunch on the steps. The girls were all in captured with Serena's mystique and Blair was left alone pouting.

He hears Nate Archibald calling his name just as he sets foot outside the school and in the courtyard, the street congested with traffic of awaiting chauffeurs. He turns around to see Nate cooly walking over to him, carrying a smirk. His long hair now covering the tips of his ears, and slight blush forming on his cheeks from the colder weather.

His entire life, he's been envious of Nate's charm.

"How's it going bro?"

He slings a bag carrying barley nothing over his shoulder. Things have been light for them ever since soccer ended. Dan can only imagine how much weed Nate has consumed.

"Good," He says, before looking over his shoulder over to the bus stop. He's kind of in a rush. "Is everything alright?"

An amused smile spreads across Nate's lips. "I went back to my locker and found an invitation to Kelly's."

He doesn't understand why it's noteworthy or why Nate has decided to share this with him. It's one of hundreds of parties there will be over the course of the year. Although he must admit it is impressive for Nate to score an invitation. Kelly's a year above them, gorgeous, and popular. Her father is a cardiologist and most of his clientele resides in the Upper East Side.

"Do you want to be my plus one?"

Serena is taking Blair so it's fairly obvious his girlfriend put Nate up to this.

He feels uneasy chills running through his body, only to see Chuck lurking around the corner. The creep is spying on them. He can't believe he has to go through this all over again. There is nothing worse than dealing with their schemes and games.

"I'm flattered." Dan smirks, placing a hand on his chest.

Nate smile levels off when he follows Dan eyes to find Chuck leaning against the ivy wall of the school building, staring their way. His jaw slackens and his demeanor changes.

"I'll see you tomorrow then?"

"Yeah, see you tomorrow," Dan answers and watches Nate walk away towards one of the awaiting town cars by the curb.

  
  
  


After helping his father with the show, he made it back to the loft with only an hour to spare before their dinner reservations. Blair told him the place just recently opened and inferred they were laid back with ID's. She also managed to get him a fake ID just in case.

He recently bought a new wardrobe with money he's made over the past two months, through using cash he's earned from his summer and investing it into stocks and gambling ventures. He bought two grand in Apple last week, confident the stock would skyrocket.

He's also finishing the last touches of his short story. His network was strong, and he knows the right people. Getting published at the age of 17 may not provide him the funds necessary for school, but he thinks it enhances his chances at a academic scholarship for Yale.

His decision for the evening is a half zip wool cosmo melange sweater and brown twill trousers. It's not quite Brook Brothers, but he thinks Blair will begrudgingly approve.

After taking a cab back to Manhattan, through the traffic, he finally makes it to the restaurant, fifteen minutes late. He sets foot into the dim candle lit room, and approaches the petite blonde hostess.

The dinner is on Blair. Serena made sure of it. Sadly, he's become charity for the privileged, but the capability of paying for dinner would only cause alarm.

He's always been quick on his feet, even out schemed Blair Waldorf once upon a time. Although falling into the trap of scheming has it's repercussions. There lies no difference amongst them if he were to become tangled in their web of deceit and manipulation. In the end, his love for Blair will remain unchanged, no matter her actions.

The blonde hostess leads him past the bar and to the main floor holding all the tables. He follows her, hands in his pockets as his nerves grow.

"Here you are." The hostess stops in front of their table and gestures him to take a seat.

Much to his surprise, Blair is there before him in a tight devil red spaghetti strap tube dress. The dress isn't formal enough for an Upper East Side party since it doesn't quite reach her knees. No, the girls are up to something much more.

Her chocolate eyes lift from the menu. "Someone needed to make the reservation."

She takes him in, lips pursed. Though, he can tell by the way she's staring at him he cleans up nicely.

His lips curl.

"Hey," He greets and pulls out a chair to take a seat in front of her. She's sitting on a booth, and there is more than enough space for Serena on the other side. "Do you have any idea when Serena's getting here?"

Serena came back to school today. She had been out of class during the past week and a half, traveling in Paris, even with finals only mere weeks away.

"No idea." Blair frowns, her dark chestnut brown curls falling over her shoulders. "Shouldn't you know?"

He's a horrible boyfriend.

"She hasn't answered any of my texts." He shrugs his shoulders.

She rolls her eyes. "Typical Serena."

"So." He places the still water back down on the table. "I hear Susie won't be attending Constance for much longer."

Blair's lips curl into a devilish smile. Susie had the audacity to make fun of Blair. Apparently, word has been slowly spreading through the halls about Nate sleeping with Serena behind Blair's back. There are only three people who originally knew, so he can't imagine finding the culprit to be difficult.

"Sometimes people need to be reminded of their place in this world."

He smirks. "Yes, we all need a good dose of humiliation once a awhile."

Her beautiful brown eyes glimmer. "Don't worry Humphrey, I'm saving the worst for your sister."

She's toying with him. Things must be going well between them.

He takes a sip from his stilled water, enjoying the cool liquid run down his throat before meeting her eyes again.

"I'll make sure to let her know."

It feels good to be able to say whatever he so chooses, not caring for the repercussions. He sees his unfazed demeanor throw her off. Over the years, he's learned when and when not to take Blair seriously. Many have tried and failed with her, but he has always been gifted with the ability to handle her quirks.

"Did you see Nelly's Trigonometry score," Blair declares, posing it as a question.

"You should respect your fellow peer's hard work and effort," He answers, hoping a light bulb will shine above that beautiful high intellect brain of hers.

She gasps at his indecency.

"Isn't it obvious," Blair asks, staring at him incredulously.

His brows furrow in confusion, as he wonders what in the world she's talking about.

"Isn't what so obvious?"

She makes an indignant sound through her throat, her disbelief in his lack of awareness.

"Nelly is having an affair," Blair announces and waits for his reaction.

He takes a sip from his glass of stilled water, praying the topic would just die away.

"So what do you think," She presses.

"I think you would make a great villain."

"Humphrey!" She whines and pouts her full lips. His lips fall victim to her adorable behavior. "Are you coming?"

"Where?"

"To the stakeout." She stares at him as though it's obvious.

"What?" A crease forms in-between his brows. It's difficult to keep up with her. "What stakeout?"

"For Nelly!"

"I'm not sure that's legal," Dan replies.

"I was only being cordial," She scoffs and folds her arms across her chest. "The nerve. And to think I was considering sharing Dorota's chocolate raspberry cheesecake with you."

"No need to throw a tantrum Waldorf, I'll go," He caves in, like always.

She beams immediately, excited for their next adventure, although being with her is enough for him. He's never wanted anything more in his life. Her death left him with dreams and deep aches.

It's obvious dealing with a younger Blair will be different, but the opportunity of letting Blair become whoever she wants without any influence is too important to him. He accepts her for who she is and is excited to see where this twisted girl takes him.

Their locked gazes break apart and Blair straightens up. His eyes wander over his shoulder to see Serena arriving at last. A sad sigh escapes his lips. He was getting somewhere with Blair.

Moment ruined in all, he stands up and manages to crack a smile, welcoming her in. Her looks are alarming. Only she could pull off black Harem pants, matching plumps, and a tight white half sleeve top.

Her kaleidoscopic bangles jingle as she approaches, warm smile spreading across her lips.

Blair arches a brow as Serena takes a seat next to her. "Where have you been?"

"Out with friends." Serena looks at him.

He swallows hard and casts his eyes down to the menu.

Sensing the tension, Blair smirks, "Who wants to order drinks?"

He orders scotch on the rocks, but he quickly learns his body isn't digesting it quite the way he remembers. Every sip is painful, causing him to wince when it burns down his throat. His tolerance is currently at a state of pathetic.

  
  
  


He's in a drunken state when they arrive in Serena's building. They took him dancing after finishing dinner. Both girls took turns rotating in, or just simply sandwiching him in-between. However, things took a dark turn when Serena snorted a line of cocaine in the bathroom with old friends.

They fought in a secluded back alley shortly after he wasn't willing to try it and the night has been tense ever sense. She thinks he is being a judgmental asshole when in fact he is afraid.

"You know, I thought you were different Dan," She slurs as he gently lays her down on the bed. Her blue eyes are full of concern.

"He is different," Blair chimes in, propping herself up from the bed to smirk at him. "He's much worse."

"Go back to sleep Waldorf," He replies and glares at her.

"Blair is right Dan, you are much worse," Serena agrees, turning around to wrap her arms around the wicked brunette.

"Let me guess, she told you about our little conversation on the MET this morning," He figures.

"Of course she did," Serena says.

All this time, right under his nose, the brunette had been playing him. How naive was it of him to believe she would want to be friends with him?

"You pretended to be my friend so you could gather dirt for Serena."

"Well duh." Blair raises both brows, smiling in victory.

Both girls straighten up, shoulders touching. They share the same unwelcoming stare. It's quite frightening to deal with them as a team.

"You don't belong here Humphrey," Blair tells him.

"Yeah, maybe you should leave," Serena adds, so sure of herself. He knows she'll regret those words tomorrow, when her head is clear.

He meets Serena's eyes, the feeling of betrayal stabbing at his heart. "Don't call me when you sober up."

Pride takes over as he turns around to leave her room, with one thought running through his head.

_Maybe he was destined to leave the Upper East Side behind_


End file.
